Pyrrolin-2-ylamino compounds for combating animal pests

ABSTRACT

The present invention relates to pyrrolin-2-ylamino compounds for combating animal pests. The invention also relates to a method for controlling animal pests by using these compounds, to plant propagation material and to an agricultural composition comprising said compounds. The invention also relates to a method for treating or protecting an animal from infestation or infection by parasites by using said compounds: 
                         
wherein:
 
A is a radical of the formulae A.1 or A.2:
 
                         
n, m, R1, R2, R3, R4, R5a, R5b, R5c, R5d, R5e, and R5f are defined herein.

This application is a National Stage application of International Application No. PCT/EP2009/061624 filed Sep. 8, 2009, which claims the benefit of U.S. Provisional Application No. 61/095,507, filed Sep. 9, 2008, the entire contents of which are hereby incorporated herein by reference.

The present invention relates to pyrrolin-2-ylamino compounds for combating animal pests. The invention also relates to a method for controlling animal pests by using these compounds, to plant propagation material and to an agricultural composition comprising said compounds. The invention also relates to a method for treating or protecting an animal from infestation or infection by parasites by using said compounds.

Animal pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwellings and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating insects, arachnids and nematodes.

Jennings et al., Pesticide Biochemistry and Physiology 30, 1988, p. 190-197 describe several (phenylamino)-oxazoline, (benzylamino)-oxazoline and (1-phenylethylamino)-oxazoline compounds which have insecticidal activity. Biosci. Biotech. Biochem. 1992, 56 (7), 1062-1065 discloses (benzylamino)-thiazoline compounds, (1-phenylethyl-amino)-thiazoline compounds and (2-phenylethylamino)-thiazoline compounds having insecticidal activity. However, these compounds are limited in their activity or with regard to the breadth of their activity spectrum.

WO 2005/063724 describe 1-(thiazolin-2-yl)amino-1,2-diphenylethane compounds and 1-(oxazolin-2-yl)amino-1,2-diphenylethane and their use for combating insects, arachnids and nematodes.

WO 2009/004032 (PCT/EP2008/058517) describes 1-(thiazolin-2-yl)amino-1,2-diphenylethane, 1-(oxazolin-2-yl)amino-1,2-diphenylethane and 1-(imidazolin-2-yl)amino-1,2-diphenylethane compounds having an insecticidal activity.

The 61/037,175 describes (azolin-2-yl)-amino-alkenyl compounds as well as agricultural compositions comprising them, which are useful for combating animal pests.

It is an object of the present invention to provide further compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different animal pests, especially against difficult to control insects.

It has been found that these objectives can be achieved by compounds of the formula I below.

Surprisingly it has been found that this object is achieved by pyrrolin-2-ylamino compounds of formula I,

wherein

-   -   n is 0, 1, 2, 3, 4 or 5;     -   m is 0, 1, 2, 3, 4 or 5;     -   R¹, R² are each independently selected from the group consisting         of:         -   halogen, CN, N₃, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl and             C₂-C₆-alkynyl, where the last 3 radicals mentioned may be             partly or completely halogenated and/or may carry any             combination of 1, 2 or 3 radicals R^(#),         -   —C(═O)R^(a), —(═S)R^(a), —C(═NR^(f))R^(a),             —C(═NR^(f))OR^(b), —C(═NR^(f))NR^(c)R^(d),             —C(═NR^(f))SR^(e), —C(═O)OR^(b), —C(═O)NR^(c)R^(d),             —C(═O)SR^(e), —(═S)OR^(b), —C(═S)NR^(c)R^(d), —(═S)SR^(e),             —OR^(b), —O—C(═O)R^(a), —O—C(═O)OR^(b),             —O—C(═O)—NR^(c)R^(d), —O—C(═O)SR^(e), —SR^(e), —S(═O)R^(e),             —S(═O)₂R^(e), —S(═O)₂OR^(b), —S(═O)₂NR^(c)R^(d),             —NR^(c)R^(d), —NR^(f)—C(═O)R^(a), —NR^(f)—C(═O)OR^(b),             —NR^(f)—C(═O)NR^(c)R^(d), —N═CR^(a)R^(a′),             —NR^(f)—NR^(c)R^(d), —NR^(f)—C(═O)SR^(e) and             —NR^(f)—(═S)NR^(c)R^(d),         -   —Y-Cy and —Y—Ar¹, wherein         -   Y is a single bond, C₁-C₆-alkanediyl, C₁-C₆-alkanediyloxy,             —C(═O)—, —(═S)—, —C(═NR^(f))—, —C(═NR^(f))O—, —C(═NR^(f))S—,             —C(═NR^(f))NR^(c), —C(═O)O—, —C(═O)NR^(c)—, —C(═O)S—,             —(═S)O—, —(═S)NR^(c)—, —(═S)S—, —O—, —O—C(═O)—, —O—C(═O)O—,             —O—C(═O)—NR^(c)—, —O—C(═O)S—, —S—, —S(═O)—, —S(═O)₂—,             —S(═O)₂O—, —S(═O)₂NR^(c)—, —NR^(c)—, —NR^(f)—C(═O)—,             —NR^(f)—C(═O)O—, —NR^(f)—C(═O)NR^(c)—, —N═CR^(a)—,             —NR^(f)—NR^(c)—, —NR^(f)—C(═O)S—, —NR^(f)—(═S)NR^(c)—,         -   Cy is C₃-C₁₂-cycloalkyl or a saturated or partially             unsaturated 5-, 6- or 7-membered heterocycle containing 1,             2, 3 or 4 heteroatoms selected independently from one             another from S, O and N as ring members, wherein             C₃-C₁₂-cycloalkyl and the heterocycle are each unsubstituted             or carry any combination of 1, 2, 3, 4 or 5 substituents             selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,             C₂-C₆-alkenyl, C₂-C₆-alkynyl and R^(#),         -   Ar¹ has one of the meanings given below,         -   and/or two radicals R¹ or two radicals R², which are bound             to adjacent carbon atoms of the phenyl ring together with             said carbon atoms form a fused 5-, 6- or 7-membered             carbocycle or a fused 5-, 6- or 7-membered heterocycle,             which contains 1, 2, 3 or 4 heteroatoms selected from O, S             and N as ring members, wherein each fused carbocycle or             heterocycle is unsubstituted or carries 1, 2, 3 or 4             substituents selected from halogen, C₁-C₆-alkyl,             C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and R^(#);     -   R³ and R⁴ are selected each independently of one another from         hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         wherein the last 3 radicals mentioned may be partly or         completely halogenated and/or may carry any combination of 1, 2         or 3 radicals selected independently of one another from the         group consisting of CN, NO₂, —OR^(b), NR^(c)R^(d), —SR^(e),         —C(═O)R^(a) and —C(═O)OR^(b),         -   C₃-C₆-cycloalkyl, phenyl and benzyl, wherein             C₃-C₆-cycloalkyl, phenyl and benzyl may carry 1, 2, 3, 4 or             5 substituents selected independently of one another from             the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl,             C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₆-haloalkyl, —OR^(b),             NR^(c)R^(d), —SR^(e), —C(═O)R^(a) and —C(═O)OR^(b);     -   A is a radical of the formulae A.1 or A.2.

-   -   -   wherein             -   indicates the point of attachment to the remaining part                 of the compound;         -   R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) are             selected independently from one another from hydrogen,             halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,             di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl and Ar², wherein             C₁-C₆-alkyl and the alkyl moiety in C₁-C₆-alkoxy,             C₁-C₆-alkylamino and di(C₁-C₆-alkyl)amino may be partially             or completely halogenated and/or may carry any combination             of 1, 2 or 3 radicals R^(#) and wherein C₃-C₆-cycloalkyl may             carry any combination of 1, 2, 3 or 4 substituents,             independently of each another being selected from             C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,             halogen and R^(#),             -   it being also possible that R^(5a) and R^(5b) or R^(5c)                 and R^(5d) or R^(5e) and R^(5f) together with the carbon                 atom to which they are bound form a 3-, 4-, 5-, 6- or                 7-membered saturated carbocycle, which is unsubstituted                 or which carries any combination of 1, 2, 3 or 4                 substituents, independently of one another selected from                 halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and                 C₂-C₆-alkynyl and R^(#);             -   it being also possible that R^(5a) and R^(5c) or R^(5d)                 and R^(5f) together with the carbon atoms to which they                 are bound form a fused 5-, 6- or 7-membered saturated,                 unsaturated or aromatic carbocycle, which is                 unsubstituted or carries any combination of 1, 2, 3 or 4                 substituents, independently of one another selected from                 halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and                 C₂-C₆-alkynyl and R^(#);

    -   R⁶ and R⁷ are selected each independently from one another from         hydrogen, CN, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₃-C₈-cycloalkyl, saturated or partially unsaturated 5-, 6- or         7-membered heterocyclic radicals, Ar³, —B—C(═O)R^(a),         —B—C(═S)R^(a), —B—C(═NR^(f))R^(a), —B—C(═NR^(f))OR^(b),         —B—C(═NR^(f))NR^(c)R^(d), —B—C(═NR^(f))SR^(e), —B—C(═O)OR^(b),         —B—C(═O)NR^(c)R^(d), —B—C(═O)SR^(e), —B—C(═S)OR^(b),         —B—C(═S)NR^(c)R^(d), —B—C(═S)SR^(e), —B—OR^(b), —B—O—C(═O)R^(a),         —B—O—C(═O)OR^(b), —B—O—C(═O)—NR^(c)R^(d), —B—O—C(═O)SR^(e),         —B—SR^(e), —B—NR^(c)R^(d), —B—NR^(f)—C(═O)R^(a),         —B—NR^(f)—C(═O)OR^(b), —B—NR^(f)—C(═O)NR^(c)R^(d),         —B—N═CR^(a)R^(a)′, —B—NR^(f)—NR^(c)R^(d), —B—NR^(f)—C(═O)SR^(e),         —B—NR^(f)—(═S)NR^(c)R^(d), —B—S(═O)R^(e), —B—S(═O)₂R^(e),         —S(═O)₂OR^(b), —S(═O)₂NR^(c)R^(d), —P(═O)R^(g)R^(h) and         P(═S)R^(g)R^(h),         -   wherein C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl may be             partly or completely halogenated and/or may carry any             combination of 1, 2, 3, 4 or 5 substituents R*,         -   wherein C₃-C₈-cycloalkyl is unsubstituted or may carry any             combination of 1, 2, 3, 4 or 5 substituents selected from             halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,             C₁-C₆-haloalkyl and R*,         -   wherein the 5-, 6- or 7-membered heterocyclic radicals             contain 1, 2, 3 or 4 heteroatoms selected independently from             one another from S, O and N as ring members, and wherein the             5-, 6- or 7-membered heterocyclic radicals are unsubstituted             or carry any combination of 1, 2, 3, 4 or 5 substituents             selected from C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,             C₁-C₆-haloalkyl, halogen and R*,         -   B is a single bond or linear or branched C₁-C₄-alkanediyl,             and R^(a), R^(a)′, R^(b), R^(c), R^(d), R^(e), R^(f), R^(g)             and R^(h) independently of one another have one of the             meanings given below,         -   R* is selected from CN, NO₂, —OR^(b), —NR^(c)R^(d), —SR^(e),             —C(═O)R^(a), —C(═O)OR^(b), C₃-C₈-cycloalkyl, saturated or             partially unsaturated 5-, 6- or 7-membered heterocyclic             radicals, —Ar⁴, —O—Ar⁴, —S—Ar⁴ and —CH₂—Ar⁴, wherein the 5-,             6- or 7-membered heterocyclic radicals contain 1, 2, 3 or 4             heteroatoms selected independently from one another from S,             O and N as ring members, and             -   wherein C₃-C₈-cycloalkyl and the heterocyclic radicals                 are unsubstituted or carry any combination of 1, 2 or 3                 or substituents, independently of one another selected                 from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,                 C₂-C₆-alkenyl and C₂-C₆-alkynyl and R^(#);

    -   R^(#) is selected from C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, CN, NO₂,         —OR^(b), —SR^(e), —NR^(c)R^(d), C(═O)—R^(a) and C(═O)OR^(b);

    -   R^(a), R^(a)′, R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and         R^(h) are independently of one another selected from hydrogen,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,         saturated or partially unsaturated 5-, 6- or 7-membered         heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms         selected independently from one another from O, S, N as ring         members, and Ar⁵,         -   wherein C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl may be             partly or completely halogenated and/or may carry any             combination of 1, 2, 3, 4 or 5 substituents, independently             of one another selected from CN, NO₂, OH, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,             C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,             C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,             C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl,             C₃-C₆-halocycloalkyl, Ar⁶, —CH₂—Ar⁶, —O—Ar⁶ and —S—Ar⁶, and             wherein C₃-C₈-cycloalkyl and the heterocyclic radicals are             unsubstituted or may carry any combination of 1, 2, 3, 4 or             5 substituents, independently of one another selected from             halogen, CN, NO₂, OH, C₁-C₆-alkyl, C₂-C₆-alkenyl,             C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,             C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,             C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,             C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,             C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl,             C₃-C₆-halocycloalkyl, Ar⁶, —CH₂—Ar⁶, —O—Ar⁶ and —S—Ar⁶;

    -   Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are independently of one another         selected from phenyl, naphthyl and mono- or bicyclic 5- to         10-membered heteroaryl, which contains 1, 2, 3 or 4 heteroatoms         selected from O, S and N as ring members, wherein phenyl,         naphthyl and heteroaryl are unsubstituted or carry any         combination of 1, 2, 3, 4 or 5 substituents R^(Ar), which are         selected from halogen, CN, NO₂, NH₂, CH₂NH₂, OH, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,         C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,         C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, unsubstituted phenyl and phenyl carrying         1, 2, 3, 4 or 5 substituents selected from halogen, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy,

and the salts thereof.

Accordingly, the present invention relates to pyrrolin-2-ylamino compounds of formula I and the salts thereof. These compounds have a high pesticidal activity and are active against a broad spectrum of animal pests, in particular invertebrate pests such as insects, arachnids and nematodes.

The present invention further relates to the use of the compounds of formula I as defined above or of a salt thereof for controlling animal pests.

The present invention also relates to an agricultural composition containing at least one compound of the formula I as defined above and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.

The present invention also relates to a method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or plants, plant propagation materials, soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of an pyrrolin-2-ylamino compound of formula I or a salt thereof.

The invention further related to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a pyrrolin-2-ylamino compound of formula I or a veterinally acceptable salt thereof.

The present invention also relates to plant propagation materials, in particular seed, comprising at least one pyrrolin-2-ylamino compound of formula I and/or an agriculturally acceptable salt thereof.

In the compounds of formula I, the carbon atom which carries the radical A creates a center of chirality. Thus, the compound of formula I may be present in the form of different enantiomers or if another center of chirality is present in any of the radicals R¹ to R⁷, it may exist in the form of diastereomers. In case that A is a radical of the formula A.2, the compound I may also exist as a cis- or trans-isomer with respect to the N═C axis. The present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxy-ethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, e.g. the monoacid salts or diacid salts of maleic acid, dimaleic acid, fumaric acid, e.g. the monoacid salts or diacid salts of fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

The term “plants” comprises any types of plants including “non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species or related species or related genera of a cultivated plant.

The term “cultivated plants” as used herein includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transitional modification of protein(s) (oligo- or polypeptides), for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001 July-August; 17(4):720-8., Protein Eng. Des. Sel. 2004 January; 17(1):57-66, Nat. Protoc. 2007; 2(5):1225-35., Curr. Opin. Chem. Biol. 2006 October; 10(5):487-91. Epub 2006 Aug. 28., Biomaterials. 2001 March; 22(5):405-17, Bioconjug Chem. 2005 January-February; 16(1):113-21).

The term “cultivated plants” as used herein further includes plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e. g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e. g. U.S. Pat. No. 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus bacillus, particularly from bacillus thuringiensis, such as endotoxins, e. g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods insects, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).

The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozyme (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

The term “cultivated plants” as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).

The term “cultivated plants” as used herein further includes plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato). The remarks made below concerning preferred embodiments of the variables of the compounds of formulae I and II, of the features of the use and method according to the invention and of the composition of the invention are valid on their own as well as preferably in combination with each other.

The term “plant propagation material” as used herein includes all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

The term “animal pests” as used herein includes all invertebrate pests which may harm or damage plants, plant propagation material, or other non-living material. The term “animal pests” as used herein includes in particular arthropods and nematodes. In the sense of the present invention, “animal pests” are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes. The term “animal pest” as used herein also encompasses ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested These pests are also referred to as invertebrate pests and include in particular insects, arachnids and nematodes.

The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

Examples of other meanings are:

The term “C₁-C₆-alkyl” as used herein and in the alkyl moieties of C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-alkylaminocarbonyl and di(C₁-C₆-alkyl)aminocarbonyl refers to a saturated straight-chain or branched hydrocarbon group having 1 to 6 carbon atoms, especially 1 to 3 carbon groups (═C₁-C₃-alkyl). Examples for C₁-C₃-alkyl are methyl, ethyl, propyl and 1-methylethyl(isopropyl). Examples for C₁-C₆-alkyl further encompass, butyl, 1-methylpropyl (sec-butyl, 2-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl(tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3 methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl.

The term “C₁-C₆-haloalkyl” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, for example C₁-C₃-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1 fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2 chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like.

The term “C₁-C₆-alkoxy” as used herein and in the terms C₁-C₆-alkoxycarbonyl and C₁-C₆-alkoxycarbonyloxy refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms (C₁-C₃-alkoxy) (as mentioned above) which is attached via an oxygen atom. Examples for C₁-C₃-alkoxy include methoxy, ethoxy, OCH₂—C₂H₅ (propoxy) and OCH(CH₃)₂ (isopropoxy). Examples for C₁-C₆-alkoxy further encompass n-butoxy, OCH(CH₃)C₂H₅ (sec-butoxy), OCH₂CH(CH₃)₂ (isobutoxy), OC(CH₃)₃ (tert-butoxy), n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-methylpropoxy and the like.

The term “C₁-C₆-haloalkoxy” as used herein refers to a C₁-C₆-alkoxy group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. Preferred are C₁-C₃-haloalkoxy groups, i.e. C₁-C₃-alkoxy groups as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy and 1-(bromomethyl)-2-bromoethoxy. Examples for C₁-C₆-haloalkoxy further encompass 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy and dodecafluorohexoxy. Particularly preferred are chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trifluoroethoxy.

The term “C₁-C₆-alkylcarbonyl” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylcarbonyl) (as mentioned above) bonded via the carbon atom of the carbonyl group at any bond in the alkyl group. Examples for C₁-C₄-alkylcarbonyl include C(O)CH₃, C(O)C₂H₅, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1,1-dimethylethylcarbonyl. Examples for C₁-C₆-alkylcarbonyl further encompass n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl and the like.

The term “C₁-C₆-alkoxycarbonyl” as used herein refers to a straight-chain or branched alkoxy group (as mentioned above) having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkoxycarbonyl) attached via the carbon atom of the carbonyl group (R—O—C(O)—; R=alkyl). Examples for C₁-C₄-alkoxycarbonyl include C(O)OCH₃, C(O)OC₂H₅, C(O)O—CH₂—C₂H₅, C(O)OCH(CH₃)₂, n-butoxycarbonyl, C(O)OCH(CH₃)—C₂H₅, C(O)OCH₂CH(CH₃)₂ and C(O)OC(CH₃)₃. Examples for C₁-C₆-alkoxycarbonyl further encompass n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3 methyl butoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3 dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2 trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl.

The term “C₁-C₆-alkylcarbonyloxy” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylcarbonyloxy) (as mentioned above) bonded via the carbon atom of the carbonyloxy group at any bond in the alkyl group. Examples for C₁-C₄-alkylcarbonyloxy include O—CO—CH₃, O—CO—C₂H₅, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-ethylpropylcarbonyloxy and 1,1-dimethylethylcarbonyloxy. Examples for C₁-C₆-alkylcarbonyloxy further encompass n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy or 1,2-dimethylpropylcarbonyloxy.

The term “C₁-C₆-alkylthio “(C₁-C₆-alkylsulfanyl: C₁-C₆-alkyl-S—)” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms (═C₁-C₃-alkylthio) (as mentioned above) which is attached via a sulfur atom. Examples for C₁-C₃-alkylthio include methylthio, ethylthio, propylthio and 1-methylethylthio. Examples for C₁-C₆-alkylthio further encompass butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio. n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-di methylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutythio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutithio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

The term “C₁-C₆-haloalkylthio” as used herein refers to a C₁-C₆-alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. Preferred are C₁-C₃-haloalkylthio groups, i.e. C₁-C₃-alkylthio groups as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoro-methylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethyl-thio, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio or 1-(bromomethyl)-2-bromoethylthio. Examples for C₁-C₆-haloalkylthio further encompass 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoro-1-pentylthio, 5-chloro-1-pentylthio, 5-bromo-1-pentylthio, 5-iodo-1-pentylthio, 5,5,5-trichloro-1-pentylthio, undecafluoropentylthio, 6-fluoro-1-hexylthio, 6-chloro-1-hexylthio, 6-bromo-1-hexylthio, 6-iodo-1-hexylthio, 6,6,6-trichloro-1-hexylthio and dodecafluorohexylthio. Particularly preferred are chloromethyl-thio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio and 2,2,2-trifluoroethylthio.

The term “C₁-C₆-alkylsulfinyl” (also referred to as C₁-C₆-alkylsulfoxyl: C₁-C₆-alkyl-S(═O)—), as used herein refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylsulfoxyl) bonded through the sulfur atom of the sulfoxyl group at any position in the alkyl group. Examples for C₁-C₄-alkylsulfoxyl include S(O)CH₃, S(O)C₂H₅, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl and 1,1-dimethylethylsulfinyl. Examples for C₁-C₆-alkylsulfinyl further encompass n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3 methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2 dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2 dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1 ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2 trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

The term “haloalkylsulfinyl” as used herein refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.

The term “C₁-C₆-alkylsulfonyl” (C₁-C₆-alkyl-S(═O)₂—) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylsulfonyl) (as mentioned above) which is bonded via the sulfur atom of the sulfonyl group at any position in the alkyl group. Examples for C₁-C₄-alkylsulfonyl include SO₂—CH₃, SO₂—C₂H₅, n-propylsulfonyl, SO₂—CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and SO₂—C(CH₃)₃. Examples for C₁-C₆-alkylsulfonyl further encompass n pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2 dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3 dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2 ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

The term “haloalkylsulfonyl” as used herein refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.

The term “C₁-C₆-alkylamino” refers to a secondary amino group carrying one alkyl group as defined above, e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino.

The term “di(C₁-C₆-alkyl)amino” refers to a tertiary amino group carrying two alkyl radicals as defined above, e.g. dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, N-ethyl-N-methylamino, N-(n-propyl)-N-methylamino, N-(isopropyl)-N-methylamino, N-(n-butyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(2-butyl)-N-methylamino, N-(isobutyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(n-propyl)-N-ethylamino, N-(isopropyl)-N-ethylamino, N-(n-butyl)-N-ethylamino, N-(n-pentyl)-N-ethylamino, N-(2-butyl)-N-ethylamino, N-(isobutyl)-N-ethylamino and the like.

The term “C₂-C₆-alkenyl” as used herein and in the alkenyl moieties of C₂-C₆-alkenyloxy, C₂-C₆-alkenylamino, C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkenyloxycarbonyl and C₂-C₆-alkenylcarbonyloxy refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2 methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1 methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2 methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3 methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3 methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3 methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3 dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3 dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1 ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term, “C₂-C₆-alkenyloxy” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via an oxygen atom, such as vinyloxy, allyloxy(propen-3-yloxy), methallyloxy, buten-4-yloxy and the like.

The term “C₂-C₆-alkenylthio” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, for example vinylsulfanyl, allylsulfanyl(propen-3-ylthio), methallylsufanyl, buten-4-ylsulfanyl and the like.

The term “C₂-C₆-alkenylcarbonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the carbonyl group at any bond in the alkenyl group, for example vinylcarbonyl, allylcarbonyl(propen-3-ylcarbonyl), methallylcarbonyl, buten-4-yl-carbonyl and the like.

The term “C₂-C₆-alkenyloxycarbonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the oxycarbonyl group (RO—C(O)—; R═C₂-C₆-alkenyl), for example vinyloxycarbonyl, allyloxycarbonyl(propen-3-yloxycarbonyl), methallyloxycarbonyl, buten-4-yloxycarbonyl and the like.

The term “C₂-C₆-alkenylcarbonyloxy” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the oxygen atom of the carbonyloxy group (R—C(O)—O—; R═C₂-C₆-alkenyl), for example vinylcarbonyloxy, allylcarbonyloxy(propen-3-ylcarbonyloxy), methallylcarbonyloxy, buten-4-ylcarbonyloxy and the like.

The term “C₂-C₆-alkenylamino” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a nitrogen atom, for example vinylamino, allylamino(propen-3-ylamino), methallylamino, buten-4-ylamino and the like.

The term “C₂-C₆-alkenylsulfonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfonyl group (SO₂), for example vinylsulfonyl, allylsulfonyl(propen-3-ylsulfonyl), methallylsufonyl, buten-4-ylsulfonyl and the like.

The term “C₂-C₆-alkynyl” as used herein and in the alkynyl moieties of C₂-C₆-alkynyloxy, C₂-C₆-alkynylamino, C₂-C₆-alkynylthio, C₂-C₆-alkynylsulfonyl, C₂-C₆-alkynylcarbonyl, C₂-C₆-alkynyloxycarbonyl and C₂-C₆-alkynyicarbonyloxy refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2 yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl and the like.

The term, “C₂-C₆-alkynyloxy” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via an oxygen atom, such as propargyloxy(propyn-3-yloxy), butyn-3-yloxy, butyn-4-yloxy and the like.

The term “C₂-C₆-alkynylthio” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, such as propargylsulfanyl(propyn-3-ylthio), butyn-3-ylsufanyl, butyn-4-ylsulfanyl and the like.

The term “C₂-C₆-alkynylcarbonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the carbonyl group at any bond in the alkynyl group, for example propargylcarbonyl(propyn-3-ylcarbonyl), butyn-3-ylcarbonyl, butyn-4-ylcarbonyl and the like.

The term “C₂-C₆-alkynyloxycarbonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the oxycarbonyl group (RO—C(O)—; R═C₂-C₆-alkynyl), for example propargyloxycarbonyl(propyn-3-yloxycarbonyl), butyn-3-yloxycarbonyl, butyn-4-yloxycarbonyl and the like.

The term “C₂-C₆-alkynylcarbonyloxy” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the oxygen atom of the carbonyloxy group (R—C(O)—O—; R═C₂-C₆-alkynyl), for example propargylcarbonyloxy(propyn-3-ylcarbonyloxy), butyn-3-ylcarbonyloxy, butyn-4-ylcarbonyloxy and the like.

The term “C₂-C₆-alkynylamino” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a nitrogen atom, such as propargylamino(propyn-3-ylamino), butyn-3-amino, butyn-4-ylamino and the like.

The term “C₂-C₆-alkynylsulfonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfonyl (SO₂) group, such as propargylsulfonyl(propin-3-yltsulfonyl), butyn-3-ylsufonyl butyn-4-ylsulfonyl and the like.

The term “C₃-C₁₂-cycloalkyl” as used herein refers to a mono- or bi- or polycyclic hydrocarbon radical having 3 to 12 (═C₃-C₁₂-cycloalkyl), frequently 3 to 8 carbon atoms (═C₃-C₈-cycloalkyl), in particular 3 to 6 carbon atoms (═C₃-C₆-cycloalkyl). Examples of monocyclic radicals comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. Examples of bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term “aryl” as used herein refers to a C₆-C₁₄ carboaromatic group, such as phenyl, naphthyl, anthracenyl and phenanthrenyl. Preferably, aryl is phenyl.

The term “aryloxy” refers to aryl as defined above which is bound via an oxygen atom to the remainder of the molecule. Examples are phenoxy and naphthoxy.

The term “arylthio” refers to aryl as defined above which is bound via a sulfur atom to the remainder of the molecule. Examples are phenoxy and naphthoxy.

Phenyl fused to phenyl is naphthyl.

Phenyl fused to a 5- or 6-membered non-aromatic (i.e. saturated or partially unsaturated) heterocyclic ring is for example 2,3-dihydrobenzofuranyl, benzoxolanyl, 2,3-dihydrobenzothienyl, indolinyl, chromanyl, chromenyl, benzodioxanyl and the like. Examples for phenyl fused to a 5- or 6-membered aromatic heterocyclic ring (=fused to a 5- or 6-membered heteroaromatic ring) are given below.

The term “heteroaryl” (“mono or bicyclic 5- to 10-membered heteroaromatic ring”) as used herein which is also referred to as “hetaryl” refers to a monocyclic heteroaromatic radical which has 5 or 6 ring members, which may be fused to a carbocyclic or heterocyclic 5-, 6- or 7-membered ring thus having a total number of ring members from 8 to 10, wherein in each case 1, 2, 3 or 4, preferably 1, 2 or 3, of these ring members are heteroatoms selected, independently from each other, from the group consisting of oxygen, nitrogen and sulfur. The heteroaryl radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. The carbocyclic or heterocyclic fused ring is selected from C₅-C₇-cycloalkyl, 5- to 7-membered heterocyclyl and phenyl.

Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl.

Examples for 5- to 6-membered heteroaromatic rings being fused to a phenyl ring (or for a phenyl ring fused to a 5- to 6-membered heteroaromatic ring) are quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzoxazolyl, and benzimidazolyl.

The term “hetaryloxy” (also referred to as heteroaryloxy) refers to hetaryl as defined above which is bound via an oxygen atom to the remainder of the molecule.

The term “hetarylthio” (also referred to as heteroarylthio) refers to hetaryl as defined above which is bound via a sulfur atom to the remainder of the molecule.

The term “heterocyclyl” (“saturated or partially unsaturated heterocycle”) comprises nonaromatic saturated or partially unsaturated heterocyclic rings having 5, 6 or 7 ring members and 1, 2, 3 or 4, preferably 1, 2 or 3 heteroatoms selected independently from one another from S, O and N as ring members. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like. Examples for heterocyclic ring also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-onyl and the like.

The term “heterocyclyloxy” refers to heterocyclyl as defined above which is bound via an oxygen atom to the remainder of the molecule.

The term “heterocyclylthio” refers to heterocyclyl as defined above which is bound via a sulfur atom to the remainder of the molecule.

The term “linear or branched C₁-C₆-alkanediyl” as used herein and in the term C₁-C₆-alkanediyloxy refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned above) in particular 1 to 4 carbon atoms (═C₁-C₄-alkanediyl), where one of the hydrogen atoms in these groups is replaced by a further bonding position. Examples for linear C₁-C₆-alkanediyl comprise methylene, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl. Examples for branched C₂-C₆-alkanediyl comprise ethane-1,1-diyl, propane-1,1-diyl, butane-1,1-diyl, 1-methylethane-1,2 diyl, 1,2-dimethylethane-1,2-diyl, 1-ethylethane-1,2 diyl, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl and the like.

The group of compounds of formula I includes compounds, wherein A is a radical of formula A.1, referred to as compounds of formula I.1 herein below, and compounds, wherein A is a radical of formula A.2, referred to as compounds of formula I.2, herein below.

The remarks made below as to preferred embodiments of the variables n, m, R¹, R², R³, R⁴, R^(5a), R^(5b), R^(5c), R^(5d), R^(5e), R^(5f) of the compounds of the formulae I, I.1 and I.2, of the features of the use and method according to the invention and of the composition of the invention are valid on their own as well as—preferably—in combination with each other.

One preferred embodiment of the invention relates to compounds of formulae I, I.1 and I.2, wherein n is 0, 1, 2 or 3, in particular 1, 2 or 3.

One preferred embodiment of the invention relates to compounds of formulae I, I.1 and I.2, wherein m is 0, 1, 2 or 3, in particular 1, 2 or 3.

According to one particular embodiment of the invention, n and m are each zero. According to a preferred embodiment of the invention, at least one of the indices n and m is different from 0. More preferably the sum n+m is an integer from 1, 2, 3, 4, 5 or 6, in particular 2, 3, 4, 5 or 6 and more preferably 3, 4 or 5.

If m and/or n is different form 0, R¹ and R² are independently of each other preferably selected from halogen, CN, substituted or unsubstistuted C₁-C₆-alkyl, substituted or unsubstistuted C₃-C₈-cycloalkyl, formyl, substituted or unsubstistuted C₁-C₆-alkylcarbonyl, —C(═O)OH, substituted or unsubstistuted C₁-C₆-alkoxycarbonyl, —C(═O)NH₂, substituted or unsubstistuted C₁-C₆-alkylaminocarbonyl, substituted or unsubstistuted di(C₁-C₆-alkyl)aminocarbonyl, —OH, substituted or unsubstistuted C₁-C₆-alkoxy, —SH, substituted or unsubstistuted C₁-C₆-alkylthio, —NH₂, substituted or unsubstistuted C₁-C₆-alkylamino and substituted or unsubstistuted di(C₁-C₆-alkyl)amino, and/or

two radicals R¹ bound to adjacent carbon atoms of the phenyl ring and/or two radicals R² bound to adjacent carbon atoms of the phenyl ring together with said carbon atoms form a fused benzene, a fused saturated or partially unsaturated 5- or 6-membered carbocycle or a fused 5- or 6-membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from O, S and N as ring members, wherein each fused benzene, carbocycle or heterocycle is unsubstituted or carries 1, 2, 3 or 4 substituents, independently of one another selected from halogen, CN, NO₂, OH, SH, NH₂, COOK C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio and C₁-C₆-haloalkylthio.

Substituted or unsubstituted C₃-C₈-cycloalkyl means that C₃-C₈-cycloalkyl is unsubstituted or may carry any combination of 1, 2 or 3 substituents as given before, where the substituents, independently of one another, are preferably selected from halogen, C₁-C₆-alkyl, CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio and C₁-C₆-haloalkylthio.

Substituted or unsubstituted alkyl and substituted or unsubstituted alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylthio, alkylamino and dialkylamino means that alkyl or the alkyl moiety of alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylthio, alkylamino and dialkylamino may be partially or completely halogenated and/or may carry any combination of 1, 2 or 3 substituents, independently of one another selected from CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio.

Particular preference is given to pyrrolin-2-ylamino compounds of formula I, wherein the radical R¹ is selected from halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, in particular chlorine or C₁-C₄-alkyl, especially methyl or ethyl. R¹ is very particularly preferably methyl. In case that n is equal to or greater than 2, R¹ may be identical or different.

Particular preference is likewise given to pyrrolin-2-ylamino compounds of formula I, wherein radical R² is, selected from halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, in particular halogen, especially chlorine, fluorine or bromine and C₁-C₄-alkyl, especially methyl or ethyl. R² is very particularly preferably methyl or chlorine. In case that m is equal to or greater than 2, R² may be identical or different.

Particular preference is likewise given to pyrrolin-2-ylamino compounds of formula I, wherein two radicals R² bound to adjacent carbon atoms of the phenyl ring together with said carbon atoms form a fused benzene or a fused 5- or 6-membered heterocycle, which contains one or two oxygen atom(s) as ring member(s), e.g. a fused tetrahydrofuran, 1,3-dioxolan or 1,4-dioxane. In this case, the fused benzene and the fused 5- or 6-membered heterocycle are particularly preferably unsubstituted or carry 1, 2, 3 or 4 substituents selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl and halogen, especially methyl and fluorine. In a most preferred embodiment of the invention, the fused benzene or 5- to 6-membered heterocycle are unsubstituted.

In principle, the radical(s) R¹ and R², if present, can be located in any position(s) on the phenyl ring. According to one particularly preferred embodiment of the invention the index m preferably is 2 or 3 and 2 radicals R¹ are located in the 3- and 5-position, relative to the bonding position, wherein R¹ has one of the meanings given before, in particular one of the preferred or more preferred meanings.

According to another particularly preferred embodiment of the invention the index n is 2 or 3 and 2 radicals R² are located in the 2- and 3-position, relative to the bonding position, wherein R² has one of the meanings given before, in particular one of the preferred or more preferred meanings.

One specific embodiment of the invention relates to pyrrolin-2-ylamino compounds of the formula I′ or the salts thereof,

wherein

A, R³ and R⁴ are as defined herein above or hereinafter;

R^(1a) and R^(1b), independently of each other, are hydrogen or have one of the meanings given for R¹ before, in particular one of the preferred or more preferred meanings,

R^(2a), R^(2b) and R^(2c), independently of each other, are hydrogen or have one of the meanings given for R² before, in particular one of the preferred or more preferred meaning.

In a more preferred embodiment of the invention, the invention relates to compounds of formula I′ or the salts thereof, wherein

-   -   R^(1a) is selected from hydrogen, halogen, C₁-C₃-alkyl,         C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, especially         halogen or C₁-C₃-alkyl, most preferred methyl;     -   R^(1b) is selected from halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,         C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, especially halogen or         C₁-C₃-alkyl, most preferred methyl;     -   R^(2a) is selected from hydrogen, halogen, C₁-C₃-alkyl,         C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, especially         halogen and C₁-C₃-alkyl, most preferred chlorine or methyl;     -   R^(2b) is selected from hydrogen, halogen, C₁-C₃-alkyl and         C₁-C₃-haloalkyl, especially halogen and C₁-C₃-alkyl, most         preferred chlorine or methyl; or     -   R^(2a) together with R^(2b) forms a bivalent radical selected         from —CH═CH—CH═CH—, —O—CH₂—CH₂—, —O—CH₂—O—, —O—CF₂—O— or         —O—CH₂—CH₂—O—, in particular —CH═CH—CH═CH—, —O—CH₂—CH₂— and         —O—CH₂—CH₂—O—;     -   R^(2c) is selected from hydrogen, halogen, C₁-C₃-alkyl,         C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, in         particular hydrogen.

Examples of more preferred compounds of formula I′ are compounds, wherein R^(1a) and R^(1b) are different from hydrogen. In another more preferred embodiment of the invention the radicals R^(2b) and R^(2c) are independently selected from hydrogen and C₁-C₃-alkyl, in particular hydrogen and methyl. Particular preferred are those compounds of formula I′, wherein R^(2a) and R^(2b) are different from hydrogen and R^(2c) is hydrogen. Also more preferred are compounds of formula I′, wherein R^(2a) together with R^(2b) forms a bivalent radical selected from —CH═CH—CH═CH—, —O—CH₂—CH₂—, —O—CH₂—O—, —O—CF₂—O— or —O—CH₂—CH₂—O—, in particular —CH═CH—CH═CH—, —O—CH₂—CH₂— and —O—CH₂—CH₂—O—.

Preferably, the radical R³ in the formulae I and I′ is hydrogen or C₁-C₆-alkyl, especially hydrogen or C₁-C₄-alkyl, in particular hydrogen or methyl and most preferably hydrogen.

The radical R⁴ in the formulae I and I′ is preferably selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last 3 radicals mentioned may be partly or completely halogenated and/or may carry any combination of 1, 2 or 3 radicals selected independently of one another from the group consisting of CN, NO₂, —OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, NH₂, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, —SH and C₁-C₆-alkylthio. More preferably, the radical R⁴ is hydrogen, halogen and C₁-C₆-alkyl, especially hydrogen, chlorine, bromine or C₁-C₄-alkyl, specially methyl or ethyl, and most preferably hydrogen.

In a further very preferred embodiment of the invention both radicals R³ and R⁴ in the formulae I and I′ are hydrogen.

According to a further preferred embodiment of the invention, the radicals R^(5a), R^(6b), R^(6c), and R^(5d), independently of one another, are selected from hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), wherein R^(Ar) has one of the meanings given before.

In one particularly preferred embodiment of the invention the radicals R^(5a), R^(5b), R^(5c) and R^(5d) are hydrogen. One particularly preferred embodiment of the invention likewise relates to compounds I, wherein R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) are hydrogen.

A further particularly preferred embodiment of the present invention relates to compounds of formula I, wherein at least one and preferably one or two of the radicals R^(5a), R^(5b), R^(5c) and R^(5d) are different from hydrogen. In this case the radicals R^(5a), R^(5b), R^(5c) and R^(5d) are selected from halogen, C₁-C₆-alkyl, especially C₁-C₄-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar). R^(Ar) has one of the meanings given before and is preferably selected from the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy. More preferably R^(Ar) is selected from bromine, chlorine, methyl, ethyl, trifluoromethyl, methoxy and trifluoromethoxy. In particular, one or two of the radicals R^(5a), R^(5b), R^(5c) and R^(5d) are selected from methyl, ethyl, unsubstituted phenyl or phenyl carrying a radical R^(Ar) in the 4-position, wherein R^(Ar) has one of the meanings given before, especially one of the preferred ones.

According to a further preferred embodiment of the invention, either R^(5a) and R^(5b) or R^(5c) and R^(5d) or R^(5e) and R^(5f) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which carries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl. In a more preferred embodiment of the invention, either R^(5a) and R^(5b) or R^(5c) and R^(5d) or R^(5e) and R^(5f) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, in particular a 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which carries any combination of 1, 2, 3 or 4 substituents, independently of one another other selected from halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl, while the remaining radicals R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) are hydrogen.

According to a preferred embodiment of the invention, the radicals R^(5e) and R^(5f), independently of one another, are selected from hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), wherein R^(Ar), has one of the meanings given before.

According to a particular preferred embodiment of the invention, the radicals R^(5e) and R^(5f) in the formulae I and I′ are hydrogen. Amongst these compounds, preference is given to those, wherein R^(5a), R^(5b), R^(5c), and R^(5d), independently of one another, are selected from hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), wherein R^(Ar) has one of the meanings given before, or R^(5a) and R^(5b) or R^(5c) and R^(5d) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which carries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl, while the remaining radicals R^(5a), R^(5b), R^(5c), R^(5d) are hydrogen.

One preferred embodiment of the invention relates to compounds of formula I, wherein R⁶ and R⁷, independently of one another, are selected from hydrogen, CN, NO₂, substituted or unsubstituted C₁-C₆-alkyl, substituted or unsubstituted C₂-C₆-alkenyl, substituted or unsubstituted C₂-C₆-alkynyl, substituted or unsubstituted C₃-C₈-cycloalkyl, —B—C(═O)R^(a), —B—C(═O)OR^(b), —B—C(═O)SR^(e), —B—C(═S)OR^(b), —B—C(═S)NR^(c) R^(d), —B—C(═S)SR^(e), —B—OR^(b), —B—SR^(e), —S(═O)R^(e), —B—NR^(c)R^(d), —S(═O)₂R^(e) and —S(═O)₂OR^(b).

If R⁶ and/or R⁷ is substituted or unsubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, then C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl may be partly or completely halogenated and/or may carry any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from CN, NO₂, —OH, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, —SH, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —C(═O)H, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms selected independently from one another from O, S, N as ring members, and —Ar⁴, wherein Ar⁴ has one of the meanings given herein.

If R⁶ and/or R⁷ is substituted or unsubstituted C₃-C₈-cycloalkyl, then C₃-C₈-cycloalky is unsubstituted or may carry any combination of 1, 2, 3 or 4 substituents, independently of one another selected from halogen, CN, NO₂, —OH, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, —SH, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —C(═O)H, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms selected independently from one another from O, S, N as ring members, —Ar⁴ and —CH₂—Ar⁴, wherein Ar⁴ has one of the meanings given herein.

If R⁶ and/or R⁷ is —B—C(═O)R^(a), —B—C(═O)OR^(b), —B—C(═O)SR^(e), —B—C(═S)OR^(b), —B—C(═S)NR^(c)R^(d), —B—C(═S)SR^(e), —B—OR^(b), —B—SR^(e), —S(═O)R^(e), —B—NR^(c)R^(d), —S(═O)₂R^(e) or —S(═O)₂OR^(b), then B is a preferably single bond or —CH₂—, and R^(a), R^(b), R^(c), R^(d) and R^(e), independently of one another, have one of the meanings given herein.

More preferably the radicals R⁶ and R⁷, independently of one another, are selected from hydrogen, CN, C₁-C₆-alkyl, —C(═O)R^(a), —C(═O)OR^(b), —OR^(b), —C(═O)SR^(e) and —B—NR^(c)R^(d), wherein C₁-C₆-alkyl may be partly or completely halogenated and/or may carry any combination of 1, 2, or 3 substituents, independently of one another selected from CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio and wherein B is a single bond or —CH₂—, and wherein R^(a), R^(b), R^(c), R^(d) and R^(e) are selected independently of one another from hydrogen, C₁-C₆-alkyl and phenyl, wherein phenyl is unsubstituted or carries 1, 2, 3, 4 or 5 substituents, independently of one another selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

In a first more preferred embodiment, R⁶ and R⁷ are hydrogen. From amongst compounds of formula I, wherein R⁶, R⁷ are different from hydrogen, more preference is given to those compounds I in which R⁶, R⁷ are cyano, formyl, C₁-C₆-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl or C₁-C₆-alkylthiocarbonyl.

The radicals R^(a), R^(a)′, R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and R^(h), if present, are preferably selected each independently of one another from hydrogen, C₁-C₆-alkyl and phenyl, wherein C₁-C₆-alkyl is unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from halogen, CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio and wherein phenyl is unsubstituted 1, 2, 3, 4 or 5 substituents, independently of one another selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

The radicals Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶, if present, are preferably independently of one another selected from naphthyl and phenyl, wherein phenyl is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

The radical Y is preferably selected from the group consisting of a single bond, C₁-C₆-alkanediyl, C₁-C₆-alkanediyloxy, —O— and —S—.

Amongst compounds I′, preference is given to those wherein A is a radical of formula A.1, in particular compounds of formula I with A being A.1, wherein R⁷ is H. These compounds are tautomers of the compounds of formula I′ with A being A.2, wherein R⁶ is hydrogen. These tautomers are present as their equilibrium mixture.

Amongst compounds of the formula I′, preference is given to the following compounds of the formula I′.1-A, wherein A is a radical A.1 with R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given above. Examples of these compounds are those wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-A.1 to I′.1-A.2798).

TABLE A R^(1a) R^(1b) R^(2a) R^(2b) R^(2c) A-1 H H H H H A-2 H F F H H A-3 H F Cl H H A-4 H F CH₃ H H A-5 H F CF₃ H H A-6 H F OCH₃ H H A-7 H F F F H A-8 H F Cl F H A-9 H F CH₃ F H A-10 H F CF₃ F H A-11 H F OCH₃ F H A-12 H F F Cl H A-13 H F Cl Cl H A-14 H F CH₃ Cl H A-15 H F CF₃ Cl H A-16 H F OCH₃ Cl H A-17 H F F CH₃ H A-18 H F Cl CH₃ H A-19 H F CH₃ CH₃ H A-20 H F CF₃ CH₃ H A-21 H F OCH₃ CH₃ H A-22 H F F CF₃ H A-23 H F Cl CF₃ H A-24 H F CH₃ CF₃ H A-25 H F CF₃ CF₃ H A-26 H F OCH₃ CF₃ H A-27 H F —O(CH₂)₂O— H A-28 H F —OCH₂CH₂—^(#) H A-29 H F —CH═CH—CH═CH— H A-30 H F F H F A-31 H F Cl H F A-32 H F CH₃ H F A-33 H F CF₃ H F A-34 H F OCH₃ H F A-35 H F F F F A-36 H F Cl F F A-37 H F CH₃ F F A-38 H F CF₃ F F A-39 H F OCH₃ F F A-40 H F F Cl F A-41 H F Cl Cl F A-42 H F CH₃ Cl F A-43 H F CF₃ Cl F A-44 H F OCH₃ Cl F A-45 H F F CH₃ F A-46 H F Cl CH₃ F A-47 H F CH₃ CH₃ F A-48 H F CF₃ CH₃ F A-49 H F OCH₃ CH₃ F A-50 H F F CF₃ F A-51 H F Cl CF₃ F A-52 H F CH₃ CF₃ F A-53 H F CF₃ CF₃ F A-54 H F OCH₃ CF₃ F A-55 H F —O(CH₂)₂O— F A-56 H F —OCH₂CH₂—^(#) F A-57 H F —CH═CH—CH═CH— F A-58 H F F H Cl A-59 H F Cl H Cl A-60 H F CH₃ H Cl A-61 H F CF₃ H Cl A-62 H F OCH₃ H Cl A-63 H F F F Cl A-64 H F Cl F Cl A-65 H F CH₃ F Cl A-66 H F CF₃ F Cl A-67 H F OCH₃ F Cl A-68 H F F Cl Cl A-69 H F Cl Cl Cl A-70 H F CH₃ Cl Cl A-71 H F CF₃ Cl Cl A-72 H F OCH₃ Cl Cl A-73 H F F CH₃ Cl A-74 H F Cl CH₃ Cl A-75 H F CH₃ CH₃ Cl A-76 H F CF₃ CH₃ Cl A-77 H F OCH₃ CH₃ Cl A-78 H F F CF₃ Cl A-79 H F Cl CF₃ Cl A-80 H F CH₃ CF₃ Cl A-81 H F CF₃ CF₃ Cl A-82 H F OCH₃ CF₃ Cl A-83 H F —O(CH₂)₂O— Cl A-84 H F —OCH₂CH₂—^(#) Cl A-85 H F —CH═CH—CH═CH— Cl A-86 H F F H CH₃ A-87 H F Cl H CH₃ A-88 H F CH₃ H CH₃ A-89 H F CF₃ H CH₃ A-90 H F OCH₃ H CH₃ A-91 H F F F CH₃ A-92 H F Cl F CH₃ A-93 H F CH₃ F CH₃ A-94 H F CF₃ F CH₃ A-95 H F OCH₃ F CH₃ A-96 H F F Cl CH₃ A-97 H F Cl Cl CH₃ A-98 H F CH₃ Cl CH₃ A-99 H F CF₃ Cl CH₃ A-100 H F OCH₃ Cl CH₃ A-101 H F F CH₃ CH₃ A-102 H F Cl CH₃ CH₃ A-103 H F CH₃ CH₃ CH₃ A-104 H F CF₃ CH₃ CH₃ A-105 H F OCH₃ CH₃ CH₃ A-106 H F F CF₃ CH₃ A-107 H F Cl CF₃ CH₃ A-108 H F CH₃ CF₃ CH₃ A-109 H F CF₃ CF₃ CH₃ A-110 H F OCH₃ CF₃ CH₃ A-111 H F —O(CH₂)₂O— CH₃ A-112 H F —OCH₂CH₂—^(#) CH₃ A-113 H F —CH═CH—CH═CH— CH₃ A-114 H F F H CF₃ A-115 H F Cl H CF₃ A-116 H F CH₃ H CF₃ A-117 H F CF₃ H CF₃ A-118 H F OCH₃ H CF₃ A-119 H F F F CF₃ A-120 H F Cl F CF₃ A-121 H F CH₃ F CF₃ A-122 H F CF₃ F CF₃ A-123 H F OCH₃ F CF₃ A-124 H F F Cl CF₃ A-125 H F Cl Cl CF₃ A-126 H F CH₃ Cl CF₃ A-127 H F CF₃ Cl CF₃ A-128 H F OCH₃ Cl CF₃ A-129 H F F CH₃ CF₃ A-130 H F Cl CH₃ CF₃ A-131 H F CH₃ CH₃ CF₃ A-132 H F CF₃ CH₃ CF₃ A-133 H F OCH₃ CH₃ CF₃ A-134 H F F CF₃ CF₃ A-135 H F Cl CF₃ CF₃ A-136 H F CH₃ CF₃ CF₃ A-137 H F CF₃ CF₃ CF₃ A-138 H F OCH₃ CF₃ CF₃ A-139 H F —O(CH₂)₂O— CF₃ A-140 H F —OCH₂CH₂—^(#) CF₃ A-141 H F —CH═CH—CH═CH— CF₃ A-142 F F F H H A-143 F F Cl H H A-144 F F CH₃ H H A-145 F F CF₃ H H A-146 F F OCH₃ H H A-147 F F F F H A-148 F F Cl F H A-149 F F CH₃ F H A-150 F F CF₃ F H A-151 F F OCH₃ F H A-152 F F F Cl H A-153 F F Cl Cl H A-154 F F CH₃ Cl H A-155 F F CF₃ Cl H A-156 F F OCH₃ Cl H A-157 F F F CH₃ H A-158 F F Cl CH₃ H A-159 F F CH₃ CH₃ H A-160 F F CF₃ CH₃ H A-161 F F OCH₃ CH₃ H A-162 F F F CF₃ H A-163 F F Cl CF₃ H A-164 F F CH₃ CF₃ H A-165 F F CF₃ CF₃ H A-166 F F OCH₃ CF₃ H A-167 F F F H F A-168 F F Cl H F A-169 F F CH₃ H F A-170 F F CF₃ H F A-171 F F OCH₃ H F A-172 F F F F F A-173 F F Cl F F A-174 F F CH₃ F F A-175 F F CF₃ F F A-176 F F OCH₃ F F A-177 F F F Cl F A-178 F F Cl Cl F A-179 F F CH₃ Cl F A-180 F F CF₃ Cl F A-181 F F OCH₃ Cl F A-182 F F F CH₃ F A-183 F F Cl CH₃ F A-184 F F CH₃ CH₃ F A-185 F F CF₃ CH₃ F A-186 F F OCH₃ CH₃ F A-187 F F F CF₃ F A-188 F F Cl CF₃ F A-189 F F CH₃ CF₃ F A-190 F F CF₃ CF₃ F A-191 F F OCH₃ CF₃ F A-192 F F —O(CH₂)₂O— F A-193 F F —OCH₂CH₂—^(#) F A-194 F F —CH═CH—CH═CH— F A-195 F F F H Cl A-196 F F Cl H Cl A-197 F F CH₃ H Cl A-198 F F CF₃ H Cl A-199 F F OCH₃ H Cl A-200 F F F F Cl A-201 F F Cl F Cl A-202 F F CH₃ F Cl A-203 F F CF₃ F Cl A-204 F F OCH₃ F Cl A-205 F F F Cl Cl A-206 F F Cl Cl Cl A-207 F F CH₃ Cl Cl A-208 F F CF₃ Cl Cl A-209 F F OCH₃ Cl Cl A-210 F F F CH₃ Cl A-211 F F Cl CH₃ Cl A-212 F F CH₃ CH₃ Cl A-213 F F CF₃ CH₃ Cl A-214 F F OCH₃ CH₃ Cl A-215 F F F CF₃ Cl A-216 F F Cl CF₃ Cl A-217 F F CH₃ CF₃ Cl A-218 F F CF₃ CF₃ Cl A-219 F F OCH₃ CF₃ Cl A-220 F F —O(CH₂)₂O— Cl A-221 F F —OCH₂CH₂—^(#) Cl A-222 F F —CH═CH—CH═CH— Cl A-223 F F F H CH₃ A-224 F F Cl H CH₃ A-225 F F CH₃ H CH₃ A-226 F F CF₃ H CH₃ A-227 F F OCH₃ H CH₃ A-228 F F F F CH₃ A-229 F F Cl F CH₃ A-230 F F CH₃ F CH₃ A-231 F F CF₃ F CH₃ A-232 F F OCH₃ F CH₃ A-233 F F F Cl CH₃ A-234 F F Cl Cl CH₃ A-235 F F CH₃ Cl CH₃ A-236 F F CF₃ Cl CH₃ A-237 F F OCH₃ Cl CH₃ A-238 F F F CH₃ CH₃ A-239 F F Cl CH₃ CH₃ A-240 F F CH₃ CH₃ CH₃ A-241 F F CF₃ CH₃ CH₃ A-242 F F OCH₃ CH₃ CH₃ A-243 F F F CF₃ CH₃ A-244 F F Cl CF₃ CH₃ A-245 F F CH₃ CF₃ CH₃ A-246 F F CF₃ CF₃ CH₃ A-247 F F OCH₃ CF₃ CH₃ A-248 F F —O(CH₂)₂O— CH₃ A-249 F F —OCH₂CH₂—^(#) CH₃ A-250 F F —CH═CH—CH═CH— CH₃ A-251 F F F H CF₃ A-252 F F Cl H CF₃ A-253 F F CH₃ H CF₃ A-254 F F CF₃ H CF₃ A-255 F F OCH₃ H CF₃ A-256 F F F F CF₃ A-257 F F Cl F CF₃ A-258 F F CH₃ F CF₃ A-259 F F CF₃ F CF₃ A-260 F F OCH₃ F CF₃ A-261 F F F Cl CF₃ A-262 F F Cl Cl CF₃ A-263 F F CH₃ Cl CF₃ A-264 F F CF₃ Cl CF₃ A-265 F F OCH₃ Cl CF₃ A-266 F F F CH₃ CF₃ A-267 F F Cl CH₃ CF₃ A-268 F F CH₃ CH₃ CF₃ A-269 F F CF₃ CH₃ CF₃ A-270 F F OCH₃ CH₃ CF₃ A-271 F F F CF₃ CF₃ A-272 F F Cl CF₃ CF₃ A-273 F F CH₃ CF₃ CF₃ A-274 F F CF₃ CF₃ CF₃ A-275 F F OCH₃ CF₃ CF₃ A-276 F F —O(CH₂)₂O— CF₃ A-277 F F —OCH₂CH₂—^(#) CF₃ A-278 F F —CH═CH—CH═CH— CF₃ A-279 Cl F F H H A-280 Cl F Cl H H A-281 Cl F CH₃ H H A-282 Cl F CF₃ H H A-283 Cl F OCH₃ H H A-284 Cl F F F H A-285 Cl F Cl F H A-286 Cl F CH₃ F H A-287 Cl F CF₃ F H A-288 Cl F OCH₃ F H A-289 Cl F F Cl H A-290 Cl F Cl Cl H A-291 Cl F CH₃ Cl H A-292 Cl F CF₃ Cl H A-293 Cl F OCH₃ Cl H A-294 Cl F F CH₃ H A-295 Cl F Cl CH₃ H A-296 Cl F CH₃ CH₃ H A-297 Cl F CF₃ CH₃ H A-298 Cl F OCH₃ CH₃ H A-299 Cl F F CF₃ H A-300 Cl F Cl CF₃ H A-301 Cl F CH₃ CF₃ H A-302 Cl F CF₃ CF₃ H A-303 Cl F OCH₃ CF₃ H A-304 Cl F —O(CH₂)₂O— H A-305 Cl F —OCH₂CH₂—^(#) H A-306 Cl F —CH═CH—CH═CH— H A-307 Cl F F H F A-308 Cl F Cl H F A-309 Cl F CH₃ H F A-310 Cl F CF₃ H F A-311 Cl F OCH₃ H F A-312 Cl F F F F A-313 Cl F Cl F F A-314 Cl F CH₃ F F A-315 Cl F CF₃ F F A-316 Cl F OCH₃ F F A-317 Cl F F Cl F A-318 Cl F Cl Cl F A-319 Cl F CH₃ Cl F A-320 Cl F CF₃ Cl F A-321 Cl F OCH₃ Cl F A-322 Cl F F CH₃ F A-323 Cl F Cl CH₃ F A-324 Cl F CH₃ CH₃ F A-325 Cl F CF₃ CH₃ F A-326 Cl F OCH₃ CH₃ F A-327 Cl F F CF₃ F A-328 Cl F Cl CF₃ F A-329 Cl F CH₃ CF₃ F A-330 Cl F CF₃ CF₃ F A-331 Cl F OCH₃ CF₃ F A-332 Cl F —O(CH₂)₂O— F A-333 Cl F —OCH₂CH₂—^(#) F A-334 Cl F —CH═CH—CH═CH— F A-335 Cl F F H Cl A-336 Cl F Cl H Cl A-337 Cl F CH₃ H Cl A-338 Cl F CF₃ H Cl A-339 Cl F OCH₃ H Cl A-340 Cl F F F Cl A-341 Cl F Cl F Cl A-342 Cl F CH₃ F Cl A-343 Cl F CF₃ F Cl A-344 Cl F OCH₃ F Cl A-345 Cl F F Cl Cl A-346 Cl F Cl Cl Cl A-347 Cl F CH₃ Cl Cl A-348 Cl F CF₃ Cl Cl A-349 Cl F OCH₃ Cl Cl A-350 Cl F F CH₃ Cl A-351 Cl F Cl CH₃ Cl A-352 Cl F CH₃ CH₃ Cl A-353 Cl F CF₃ CH₃ Cl A-354 Cl F OCH₃ CH₃ Cl A-355 Cl F F CF₃ Cl A-356 Cl F Cl CF₃ Cl A-357 Cl F CH₃ CF₃ Cl A-358 Cl F CF₃ CF₃ Cl A-359 Cl F OCH₃ CF₃ Cl A-360 Cl F —O(CH₂)₂O— Cl A-361 Cl F —OCH₂CH₂—^(#) Cl A-362 Cl F —CH═CH—CH═CH— Cl A-363 Cl F F H CH₃ A-364 Cl F Cl H CH₃ A-365 Cl F CH₃ H CH₃ A-366 Cl F CF₃ H CH₃ A-367 Cl F OCH₃ H CH₃ A-368 Cl F F F CH₃ A-369 Cl F Cl F CH₃ A-370 Cl F CH₃ F CH₃ A-371 Cl F CF₃ F CH₃ A-372 Cl F OCH₃ F CH₃ A-373 Cl F F Cl CH₃ A-374 Cl F Cl Cl CH₃ A-375 Cl F CH₃ Cl CH₃ A-376 Cl F CF₃ Cl CH₃ A-377 Cl F OCH₃ Cl CH₃ A-378 Cl F F CH₃ CH₃ A-379 Cl F Cl CH₃ CH₃ A-380 Cl F CH₃ CH₃ CH3 A-381 Cl F CF₃ CH₃ CH₃ A-382 Cl F OCH₃ CH₃ CH₃ A-383 Cl F F CF₃ CH₃ A-384 Cl F Cl CF₃ CH₃ A-385 Cl F CH₃ CF₃ CH₃ A-386 Cl F CF₃ CF₃ CH₃ A-387 Cl F OCH₃ CF₃ CH₃ A-388 Cl F —O(CH₂)₂O— CH₃ A-389 Cl F —OCH₂CH₂—^(#) CH₃ A-390 Cl F —CH═CH—CH═CH— CH₃ A-391 Cl F F H CF₃ A-392 Cl F Cl H CF₃ A-393 Cl F CH₃ H CF₃ A-394 Cl F CF₃ H CF₃ A-395 Cl F OCH₃ H CF₃ A-396 Cl F F F CF₃ A-397 Cl F Cl F CF₃ A-398 Cl F CH₃ F CF₃ A-399 Cl F CF₃ F CF₃ A-400 Cl F OCH₃ F CF₃ A-401 Cl F F Cl CF₃ A-402 Cl F Cl Cl CF₃ A-403 Cl F CH₃ Cl CF₃ A-404 Cl F CF₃ Cl CF₃ A-405 Cl F OCH₃ Cl CF₃ A-406 Cl F F CH₃ CF₃ A-407 Cl F Cl CH₃ CF₃ A-408 Cl F CH₃ CH₃ CF₃ A-409 Cl F CF₃ CH₃ CF₃ A-410 Cl F OCH₃ CH₃ CF₃ A-411 Cl F F CF₃ CF₃ A-412 Cl F Cl CF₃ CF₃ A-413 Cl F CH₃ CF₃ CF₃ A-414 Cl F CF₃ CF₃ CF₃ A-415 Cl F OCH₃ CF₃ CF₃ A-416 Cl F —O(CH₂)₂O— CF₃ A-417 Cl F —OCH₂CH₂—^(#) CF₃ A-418 Cl F —CH═CH—CH═CH— CF₃ A-419 CH₃ F F H H A-420 CH₃ F Cl H H A-421 CH₃ F CH₃ H H A-422 CH₃ F CF₃ H H A-423 CH₃ F OCH₃ H H A-424 CH₃ F F F H A-425 CH₃ F Cl F H A-426 CH₃ F CH₃ F H A-427 CH₃ F CF₃ F H A-428 CH₃ F OCH₃ F H A-429 CH₃ F F Cl H A-430 CH₃ F Cl Cl H A-431 CH₃ F CH₃ Cl H A-432 CH₃ F CF₃ Cl H A-433 CH₃ F OCH₃ Cl H A-434 CH₃ F F CH₃ H A-435 CH₃ F Cl CH₃ H A-436 CH₃ F CH₃ CH₃ H A-437 CH₃ F CF₃ CH₃ H A-438 CH₃ F OCH₃ CH₃ H A-439 CH₃ F F CF₃ H A-440 CH₃ F Cl CF₃ H A-441 CH₃ F CH₃ CF₃ H A-442 CH₃ F CF₃ CF₃ H A-443 CH₃ F OCH₃ CF₃ H A-444 CH₃ F —O(CH₂)₂O— H A-445 CH₃ F —OCH₂CH₂—^(#) H A-446 CH₃ F —CH═CH—CH═CH— H A-447 CH₃ F F H F A-448 CH₃ F Cl H F A-449 CH₃ F CH₃ H F A-450 CH₃ F CF₃ H F A-451 CH₃ F OCH₃ H F A-452 CH₃ F F F F A-453 CH₃ F Cl F F A-454 CH₃ F CH₃ F F A-455 CH₃ F CF₃ F F A-456 CH₃ F OCH₃ F F A-457 CH₃ F F Cl F A-458 CH₃ F Cl Cl F A-459 CH₃ F CH₃ Cl F A-460 CH₃ F CF₃ Cl F A-461 CH₃ F OCH₃ Cl F A-462 CH₃ F F CH₃ F A-463 CH₃ F Cl CH₃ F A-464 CH₃ F CH₃ CH₃ F A-465 CH₃ F CF₃ CH₃ F A-466 CH₃ F OCH₃ CH₃ F A-467 CH₃ F F CF₃ F A-468 CH₃ F Cl CF₃ F A-469 CH₃ F CH₃ CF₃ F A-470 CH₃ F CF₃ CF₃ F A-471 CH₃ F OCH₃ CF₃ F A-472 CH₃ F —O(CH₂)₂O— F A-473 CH₃ F —OCH₂CH₂—^(#) F A-474 CH₃ F —CH═CH—CH═CH— F A-475 CH₃ F F H Cl A-476 CH₃ F Cl H Cl A-477 CH₃ F CH₃ H Cl A-478 CH₃ F CF₃ H Cl A-479 CH₃ F OCH₃ H Cl A-480 CH₃ F F F Cl A-481 CH₃ F Cl F Cl A-482 CH₃ F CH₃ F Cl A-483 CH₃ F CF₃ F Cl A-484 CH₃ F OCH₃ F Cl A-485 CH₃ F F Cl Cl A-486 CH₃ F Cl Cl Cl A-487 CH₃ F CH₃ Cl Cl A-488 CH₃ F CF₃ Cl Cl A-489 CH₃ F OCH₃ Cl Cl A-490 CH₃ F F CH₃ Cl A-491 CH₃ F Cl CH₃ Cl A-492 CH₃ F CH₃ CH₃ Cl A-493 CH₃ F CF₃ CH₃ Cl A-494 CH₃ F OCH₃ CH₃ Cl A-495 CH₃ F F CF₃ Cl A-496 CH₃ F Cl CF₃ Cl A-497 CH₃ F CH₃ CF₃ Cl A-498 CH₃ F CF₃ CF₃ Cl A-499 CH₃ F OCH₃ CF₃ Cl A-500 CH₃ F —O(CH₂)₂O— Cl A-501 CH₃ F —OCH₂CH₂—^(#) Cl A-502 CH₃ F —CH═CH—CH═CH— Cl A-503 CH₃ F F H CH₃ A-504 CH₃ F Cl H CH₃ A-505 CH₃ F CH₃ H CH₃ A-506 CH₃ F CF₃ H CH₃ A-507 CH₃ F OCH₃ H CH₃ A-508 CH₃ F F F CH₃ A-509 CH₃ F Cl F CH₃ A-510 CH₃ F CH₃ F CH₃ A-511 CH₃ F CF₃ F CH₃ A-512 CH₃ F OCH₃ F CH₃ A-513 CH₃ F F Cl CH₃ A-514 CH₃ F Cl Cl CH₃ A-515 CH₃ F CH₃ Cl CH₃ A-516 CH₃ F CF₃ Cl CH₃ A-517 CH₃ F OCH₃ Cl CH₃ A-518 CH₃ F F CH₃ CH₃ A-519 CH₃ F Cl CH₃ CH₃ A-520 CH₃ F CH₃ CH₃ CH₃ A-521 CH₃ F CF₃ CH₃ CH₃ A-522 CH₃ F OCH₃ CH₃ CH₃ A-523 CH₃ F F CF₃ CH₃ A-524 CH₃ F Cl CF₃ CH₃ A-525 CH₃ F CH₃ CF₃ CH₃ A-526 CH₃ F CF₃ CF₃ CH₃ A-527 CH₃ F OCH₃ CF₃ CH₃ A-528 CH₃ F —O(CH₂)₂O— CH₃ A-529 CH₃ F —OCH₂CH₂—^(#) CH₃ A-530 CH₃ F —CH═CH—CH═CH— CH₃ A-531 CH₃ F F H CF₃ A-532 CH₃ F Cl H CF₃ A-533 CH₃ F CH₃ H CF₃ A-534 CH₃ F CF₃ H CF₃ A-535 CH₃ F OCH₃ H CF₃ A-536 CH₃ F F F CF₃ A-537 CH₃ F Cl F CF₃ A-538 CH₃ F CH₃ F CF₃ A-539 CH₃ F CF₃ F CF₃ A-540 CH₃ F OCH₃ F CF₃ A-541 CH₃ F F Cl CF₃ A-542 CH₃ F Cl Cl CF₃ A-543 CH₃ F CH₃ Cl CF₃ A-544 CH₃ F CF₃ Cl CF₃ A-545 CH₃ F OCH₃ Cl CF₃ A-546 CH₃ F F CH₃ CF₃ A-547 CH₃ F Cl CH₃ CF₃ A-548 CH₃ F CH₃ CH₃ CF₃ A-549 CH₃ F CF₃ CH₃ CF₃ A-550 CH₃ F OCH₃ CH₃ CF₃ A-551 CH₃ F F CF₃ CF₃ A-552 CH₃ F Cl CF₃ CF₃ A-553 CH₃ F CH₃ CF₃ CF₃ A-554 CH₃ F CF₃ CF₃ CF3 A-555 CH₃ F OCH₃ CF₃ CF₃ A-556 CH₃ F —O(CH₂)₂O— CF₃ A-557 CH₃ F —OCH₂CH₂—^(#) CF₃ A-558 CH₃ F —CH═CH—CH═CH— CF₃ A-559 CF₃ F F H H A-560 CF₃ F Cl H H A-561 CF₃ F CH₃ H H A-562 CF₃ F CF₃ H H A-563 CF₃ F OCH₃ H H A-564 CF₃ F F F H A-565 CF₃ F Cl F H A-566 CF₃ F CH₃ F H A-567 CF₃ F CF₃ F H A-568 CF₃ F OCH₃ F H A-569 CF₃ F F Cl H A-570 CF₃ F Cl Cl H A-571 CF₃ F CH₃ Cl H A-572 CF₃ F CF₃ Cl H A-573 CF₃ F OCH₃ Cl H A-574 CF₃ F F CH₃ H A-575 CF₃ F Cl CH₃ H A-576 CF₃ F CH₃ CH₃ H A-577 CF₃ F CF₃ CH₃ H A-578 CF₃ F OCH₃ CH₃ H A-579 CF₃ F F CF₃ H A-580 CF₃ F Cl CF₃ H A-581 CF₃ F CH₃ CF₃ H A-582 CF₃ F CF₃ CF₃ H A-583 CF₃ F OCH₃ CF₃ H A-584 CF₃ F —O(CH₂)₂O— H A-585 CF₃ F —OCH₂CH₂—^(#) H A-586 CF₃ F —CH═CH—CH═CH— H A-587 CF₃ F F H F A-588 CF₃ F Cl H F A-589 CF₃ F CH₃ H F A-590 CF₃ F CF₃ H F A-591 CF₃ F OCH₃ H F A-592 CF₃ F F F F A-593 CF₃ F Cl F F A-594 CF₃ F CH₃ F F A-595 CF₃ F CF₃ F F A-596 CF₃ F OCH₃ F F A-597 CF₃ F F Cl F A-598 CF₃ F Cl Cl F A-599 CF₃ F CH₃ Cl F A-600 CF₃ F CF₃ Cl F A-601 CF₃ F OCH₃ Cl F A-602 CF₃ F F CH₃ F A-603 CF₃ F Cl CH₃ F A-604 CF₃ F CH₃ CH₃ F A-605 CF₃ F CF₃ CH₃ F A-606 CF₃ F OCH₃ CH₃ F A-607 CF₃ F F CF₃ F A-608 CF₃ F Cl CF₃ F A-609 CF₃ F CH₃ CF₃ F A-610 CF₃ F CF₃ CF₃ F A-611 CF₃ F OCH₃ CF₃ F A-612 CF₃ F —O(CH₂)₂O— F A-613 CF₃ F —OCH₂CH₂—^(#) F A-614 CF₃ F —CH═CH—CH═CH— F A-615 CF₃ F F H Cl A-616 CF₃ F Cl H Cl A-617 CF₃ F CH₃ H Cl A-618 CF₃ F CF₃ H Cl A-619 CF₃ F OCH₃ H Cl A-620 CF₃ F F F Cl A-621 CF₃ F Cl F Cl A-622 CF₃ F CH₃ F Cl A-623 CF₃ F CF₃ F Cl A-624 CF₃ F OCH₃ F Cl A-625 CF₃ F F Cl Cl A-626 CF₃ F Cl Cl Cl A-627 CF₃ F CH₃ Cl Cl A-628 CF₃ F CF₃ Cl Cl A-629 CF₃ F OCH₃ Cl Cl A-630 CF₃ F F CH₃ Cl A-631 CF₃ F Cl CH₃ Cl A-632 CF₃ F CH₃ CH₃ Cl A-633 CF₃ F CF₃ CH₃ Cl A-634 CF₃ F OCH₃ CH₃ Cl A-635 CF₃ F F CF₃ Cl A-636 CF₃ F Cl CF₃ Cl A-637 CF₃ F CH₃ CF₃ Cl A-638 CF₃ F CF₃ CF₃ Cl A-639 CF₃ F OCH₃ CF₃ Cl A-640 CF₃ F —O(CH₂)₂O— Cl A-641 CF₃ F —OCH₂CH₂—^(#) Cl A-642 CF₃ F —CH═CH—CH═CH— Cl A-643 CF₃ F F H CH₃ A-644 CF₃ F Cl H CH₃ A-645 CF₃ F CH₃ H CH₃ A-646 CF₃ F CF₃ H CH₃ A-647 CF₃ F OCH₃ H CH₃ A-648 CF₃ F F F CH₃ A-649 CF₃ F Cl F CH₃ A-650 CF₃ F CH₃ F CH₃ A-651 CF₃ F CF₃ F CH₃ A-652 CF₃ F OCH₃ F CH₃ A-653 CF₃ F F Cl CH₃ A-654 CF₃ F Cl Cl CH₃ A-655 CF₃ F CH₃ Cl CH₃ A-656 CF₃ F CF₃ Cl CH₃ A-657 CF₃ F OCH₃ Cl CH₃ A-658 CF₃ F F CH₃ CH₃ A-659 CF₃ F Cl CH₃ CH₃ A-660 CF₃ F CH₃ CH₃ CH₃ A-661 CF₃ F CF₃ CH₃ CH₃ A-662 CF₃ F OCH₃ CH₃ CH₃ A-663 CF₃ F F CF₃ CH₃ A-664 CF₃ F Cl CF₃ CH₃ A-665 CF₃ F CH₃ CF₃ CH₃ A-666 CF₃ F CF₃ CF₃ CH₃ A-667 CF₃ F OCH₃ CF₃ CH₃ A-668 CF₃ F —O(CH₂)₂O— CH₃ A-669 CF₃ F —OCH₂CH₂—^(#) CH₃ A-670 CF₃ F —CH═CH—CH═CH— CH₃ A-671 CF₃ F F H CF₃ A-672 CF₃ F Cl H CF₃ A-673 CF₃ F CH₃ H CF₃ A-674 CF₃ F CF₃ H CF₃ A-675 CF₃ F OCH₃ H CF₃ A-676 CF₃ F F F CF₃ A-677 CF₃ F Cl F CF₃ A-678 CF₃ F CH₃ F CF₃ A-679 CF₃ F CF₃ F CF₃ A-680 CF₃ F OCH₃ F CF₃ A-681 CF₃ F F Cl CF₃ A-682 CF₃ F Cl Cl CF₃ A-683 CF₃ F CH₃ Cl CF₃ A-684 CF₃ F CF₃ Cl CF₃ A-685 CF₃ F OCH₃ Cl CF₃ A-686 CF₃ F F CH₃ CF₃ A-687 CF₃ F Cl CH₃ CF₃ A-688 CF₃ F CH₃ CH₃ CF₃ A-689 CF₃ F CF₃ CH₃ CF₃ A-690 CF₃ F OCH₃ CH₃ CF₃ A-691 CF₃ F F CF₃ CF₃ A-692 CF₃ F Cl CF₃ CF₃ A-693 CF₃ F CH₃ CF₃ CF₃ A-694 CF₃ F CF₃ CF₃ CF3 A-695 CF₃ F OCH₃ CF₃ CF₃ A-696 CF₃ F —O(CH₂)₂O— CF₃ A-697 CF₃ F —OCH₂CH₂—^(#) CF₃ A-698 CF₃ F —CH═CH—CH═CH— CF₃ A-699 H Cl F H H A-700 H Cl Cl H H A-701 H Cl CH₃ H H A-702 H Cl CF₃ H H A-703 H Cl OCH₃ H H A-704 H Cl F F H A-705 H Cl Cl F H A-706 H Cl CH₃ F H A-707 H Cl CF₃ F H A-708 H Cl OCH₃ F H A-709 H Cl F Cl H A-710 H Cl Cl Cl H A-711 H Cl CH₃ Cl H A-712 H Cl CF₃ Cl H A-713 H Cl OCH₃ Cl H A-714 H Cl F CH₃ H A-715 H Cl Cl CH₃ H A-716 H Cl CH₃ CH₃ H A-717 H Cl CF₃ CH₃ H A-718 H Cl OCH₃ CH₃ H A-719 H Cl F CF₃ H A-720 H Cl Cl CF₃ H A-721 H Cl CH₃ CF₃ H A-722 H Cl CF₃ CF₃ H A-723 H Cl OCH₃ CF₃ H A-724 H Cl —O(CH₂)₂O— H A-725 H Cl —OCH₂CH₂—^(#) H A-726 H Cl —CH═CH—CH═CH— H A-727 H Cl F H F A-728 H Cl Cl H F A-729 H Cl CH₃ H F A-730 H Cl CF₃ H F A-731 H Cl OCH₃ H F A-732 H Cl F F F A-733 H Cl Cl F F A-734 H Cl CH₃ F F A-735 H Cl CF₃ F F A-736 H Cl OCH₃ F F A-737 H Cl F Cl F A-738 H Cl Cl Cl F A-739 H Cl CH₃ Cl F A-740 H Cl CF₃ Cl F A-741 H Cl OCH₃ Cl F A-742 H Cl F CH₃ F A-743 H Cl Cl CH₃ F A-744 H Cl CH₃ CH₃ F A-745 H Cl CF₃ CH₃ F A-746 H Cl OCH₃ CH₃ F A-747 H Cl F CF₃ F A-748 H Cl Cl CF₃ F A-749 H Cl CH₃ CF₃ F A-750 H Cl CF₃ CF₃ F A-751 H Cl OCH₃ CF₃ F A-752 H Cl —O(CH₂)₂O— F A-753 H Cl —OCH₂CH₂—^(#) F A-754 H Cl —CH═CH—CH═CH— F A-755 H Cl F H Cl A-756 H Cl Cl H Cl A-757 H Cl CH₃ H Cl A-758 H Cl CF₃ H Cl A-759 H Cl OCH₃ H Cl A-760 H Cl F F Cl A-761 H Cl Cl F Cl A-762 H Cl CH₃ F Cl A-763 H Cl CF₃ F Cl A-764 H Cl OCH₃ F Cl A-765 H Cl F Cl Cl A-766 H Cl Cl Cl Cl A-767 H Cl CH₃ Cl Cl A-768 H Cl CF₃ Cl Cl A-769 H Cl OCH₃ Cl Cl A-770 H Cl F CH₃ Cl A-771 H Cl Cl CH₃ Cl A-772 H Cl CH₃ CH₃ Cl A-773 H Cl CF₃ CH₃ Cl A-774 H Cl OCH₃ CH₃ Cl A-775 H Cl F CF₃ Cl A-776 H Cl Cl CF₃ Cl A-777 H Cl CH₃ CF₃ Cl A-778 H Cl CF₃ CF₃ Cl A-779 H Cl OCH₃ CF₃ Cl A-780 H Cl —O(CH₂)₂O— Cl A-781 H Cl —OCH₂CH₂—^(#) Cl A-782 H Cl —CH═CH—CH═CH— Cl A-783 H Cl F H CH₃ A-784 H Cl Cl H CH₃ A-785 H Cl CH₃ H CH₃ A-786 H Cl CF₃ H CH₃ A-787 H Cl OCH₃ H CH₃ A-788 H Cl F F CH₃ A-789 H Cl Cl F CH₃ A-790 H Cl CH₃ F CH₃ A-791 H Cl CF₃ F CH₃ A-792 H Cl OCH₃ F CH₃ A-793 H Cl F Cl CH₃ A-794 H Cl Cl Cl CH₃ A-795 H Cl CH₃ Cl CH₃ A-796 H Cl CF₃ Cl CH₃ A-797 H Cl OCH₃ Cl CH₃ A-798 H Cl F CH₃ CH₃ A-799 H Cl Cl CH₃ CH₃ A-800 H Cl CH₃ CH₃ CH₃ A-801 H Cl CF₃ CH₃ CH₃ A-802 H Cl OCH₃ CH₃ CH₃ A-803 H Cl F CF₃ CH₃ A-804 H Cl Cl CF₃ CH₃ A-805 H Cl CH₃ CF₃ CH₃ A-806 H Cl CF₃ CF₃ CH₃ A-807 H Cl OCH₃ CF₃ CH₃ A-808 H Cl —O(CH₂)₂O— CH₃ A-809 H Cl —OCH₂CH₂—^(#) CH₃ A-810 H Cl —CH═CH—CH═CH— CH₃ A-811 H Cl F H CF₃ A-812 H Cl Cl H CF₃ A-813 H Cl CH₃ H CF₃ A-814 H Cl CF₃ H CF₃ A-815 H Cl OCH₃ H CF₃ A-816 H Cl F F CF₃ A-817 H Cl Cl F CF₃ A-818 H Cl CH₃ F CF₃ A-819 H Cl CF₃ F CF₃ A-820 H Cl OCH₃ F CF₃ A-821 H Cl F Cl CF₃ A-822 H Cl Cl Cl CF₃ A-823 H Cl CH₃ Cl CF₃ A-824 H Cl CF₃ Cl CF₃ A-825 H Cl OCH₃ Cl CF₃ A-826 H Cl F CH₃ CF₃ A-827 H Cl Cl CH₃ CF₃ A-828 H Cl CH₃ CH₃ CF₃ A-829 H Cl CF₃ CH₃ CF₃ A-830 H Cl OCH₃ CH₃ CF₃ A-831 H Cl F CF₃ CF₃ A-832 H Cl Cl CF₃ CF₃ A-833 H Cl CH₃ CF₃ CF₃ A-834 H Cl CF₃ CF₃ CF₃ A-835 H Cl OCH₃ CF₃ CF₃ A-836 H Cl —O(CH₂)₂O— CF₃ A-837 H Cl —OCH₂CH₂—^(#) CF₃ A-838 H Cl —CH═CH—CH═CH— CF₃ A-839 F Cl F H H A-840 F Cl Cl H H A-841 F Cl CH₃ H H A-842 F Cl CF₃ H H A-843 F Cl OCH₃ H H A-844 F Cl F F H A-845 F Cl Cl F H A-846 F Cl CH₃ F H A-847 F Cl CF₃ F H A-848 F Cl OCH₃ F H A-849 F Cl F Cl H A-850 F Cl Cl Cl H A-851 F Cl CH₃ Cl H A-852 F Cl CF₃ Cl H A-853 F Cl OCH₃ Cl H A-854 F Cl F CH₃ H A-855 F Cl Cl CH₃ H A-856 F Cl CH₃ CH₃ H A-857 F Cl CF₃ CH₃ H A-858 F Cl OCH₃ CH₃ H A-859 F Cl F CF₃ H A-860 F Cl Cl CF₃ H A-861 F Cl CH₃ CF₃ H A-862 F Cl CF₃ CF₃ H A-863 F Cl OCH₃ CF₃ H A-864 F Cl —O(CH₂)₂O— H A-865 F Cl —OCH₂CH₂—^(#) H A-866 F Cl —CH═CH—CH═CH— H A-867 F Cl F H F A-868 F Cl Cl H F A-869 F Cl CH₃ H F A-870 F Cl CF₃ H F A-871 F Cl OCH₃ H F A-872 F Cl F F F A-873 F Cl Cl F F A-874 F Cl CH₃ F F A-875 F Cl CF₃ F F A-876 F Cl OCH₃ F F A-877 F Cl F Cl F A-878 F Cl Cl Cl F A-879 F Cl CH₃ Cl F A-880 F Cl CF₃ Cl F A-881 F Cl OCH₃ Cl F A-882 F Cl F CH₃ F A-883 F Cl Cl CH₃ F A-884 F Cl CH₃ CH₃ F A-885 F Cl CF₃ CH₃ F A-886 F Cl OCH₃ CH₃ F A-887 F Cl F CF₃ F A-888 F Cl Cl CF₃ F A-889 F Cl CH₃ CF₃ F A-890 F Cl CF₃ CF₃ F A-891 F Cl OCH₃ CF₃ F A-892 F Cl —O(CH₂)₂O— F A-893 F Cl —OCH₂CH₂—^(#) F A-894 F Cl —CH═CH—CH═CH— F A-895 F Cl F H Cl A-896 F Cl Cl H Cl A-897 F Cl CH₃ H Cl A-898 F Cl CF₃ H Cl A-899 F Cl OCH₃ H Cl A-900 F Cl F F Cl A-901 F Cl Cl F Cl A-902 F Cl CH₃ F Cl A-903 F Cl CF₃ F Cl A-904 F Cl OCH₃ F Cl A-905 F Cl F Cl Cl A-906 F Cl Cl Cl Cl A-907 F Cl CH₃ Cl Cl A-908 F Cl CF₃ Cl Cl A-909 F Cl OCH₃ Cl Cl A-910 F Cl F CH₃ Cl A-911 F Cl Cl CH₃ Cl A-912 F Cl CH₃ CH₃ Cl A-913 F Cl CF₃ CH₃ Cl A-914 F Cl OCH₃ CH₃ Cl A-915 F Cl F CF₃ Cl A-916 F Cl Cl CF₃ Cl A-917 F Cl CH₃ CF₃ Cl A-918 F Cl CF₃ CF₃ Cl A-919 F Cl OCH₃ CF₃ Cl A-920 F Cl —O(CH₂)₂O— Cl A-921 F Cl —OCH₂CH₂—^(#) Cl A-922 F Cl —CH═CH—CH═CH— Cl A-923 F Cl F H CH₃ A-924 F Cl Cl H CH₃ A-925 F Cl CH₃ H CH₃ A-926 F Cl CF₃ H CH₃ A-927 F Cl OCH₃ H CH₃ A-928 F Cl F F CH₃ A-929 F Cl Cl F CH₃ A-930 F Cl CH₃ F CH₃ A-931 F Cl CF₃ F CH₃ A-932 F Cl OCH₃ F CH₃ A-933 F Cl F Cl CH₃ A-934 F Cl Cl Cl CH₃ A-935 F Cl CH₃ Cl CH₃ A-936 F Cl CF₃ Cl CH₃ A-937 F Cl OCH₃ Cl CH₃ A-938 F Cl F CH₃ CH₃ A-939 F Cl Cl CH₃ CH₃ A-940 F Cl CH₃ CH₃ CH₃ A-941 F Cl CF₃ CH₃ CH₃ A-942 F Cl OCH₃ CH₃ CH₃ A-943 F Cl F CF₃ CH₃ A-944 F Cl Cl CF₃ CH₃ A-945 F Cl CH₃ CF₃ CH₃ A-946 F Cl CF₃ CF₃ CH₃ A-947 F Cl OCH₃ CF₃ CH₃ A-948 F Cl —O(CH₂)₂O— CH₃ A-949 F Cl —OCH₂CH₂—^(#) CH₃ A-950 F Cl —CH═CH—CH═CH— CH₃ A-951 F Cl F H CF₃ A-952 F Cl Cl H CF₃ A-953 F Cl CH₃ H CF₃ A-954 F Cl CF₃ H CF₃ A-955 F Cl OCH₃ H CF₃ A-956 F Cl F F CF₃ A-957 F Cl Cl F CF₃ A-958 F Cl CH₃ F CF₃ A-959 F Cl CF₃ F CF₃ A-960 F Cl OCH₃ F CF₃ A-961 F Cl F Cl CF₃ A-962 F Cl Cl Cl CF₃ A-963 F Cl CH₃ Cl CF₃ A-964 F Cl CF₃ Cl CF₃ A-965 F Cl OCH₃ Cl CF₃ A-966 F Cl F CH₃ CF₃ A-967 F Cl Cl CH₃ CF₃ A-968 F Cl CH₃ CH₃ CF₃ A-969 F Cl CF₃ CH₃ CF₃ A-970 F Cl OCH₃ CH₃ CF₃ A-971 F Cl F CF₃ CF₃ A-972 F Cl Cl CF₃ CF₃ A-973 F Cl CH₃ CF₃ CF₃ A-974 F Cl CF₃ CF₃ CF₃ A-975 F Cl OCH₃ CF₃ CF₃ A-976 F Cl —O(CH₂)₂O— CF₃ A-977 F Cl —OCH₂CH₂—^(#) CF₃ A-978 F Cl —CH═CH—CH═CH— CF₃ A-979 Cl Cl F H H A-980 Cl Cl Cl H H A-981 Cl Cl CH₃ H H A-982 Cl Cl CF₃ H H A-983 Cl Cl OCH₃ H H A-984 Cl Cl F F H A-985 Cl Cl Cl F H A-986 Cl Cl CH₃ F H A-987 Cl Cl CF₃ F H A-988 Cl Cl OCH₃ F H A-989 Cl Cl F Cl H A-990 Cl Cl Cl Cl H A-991 Cl Cl CH₃ Cl H A-992 Cl Cl CF₃ Cl H A-993 Cl Cl OCH₃ Cl H A-994 Cl Cl F CH₃ H A-995 Cl Cl Cl CH₃ H A-996 Cl Cl CH₃ CH₃ H A-997 Cl Cl CF₃ CH₃ H A-998 Cl Cl OCH₃ CH₃ H A-999 Cl Cl F CF₃ H A-1000 Cl Cl Cl CF₃ H A-1001 Cl Cl CH₃ CF₃ H A-1002 Cl Cl CF₃ CF₃ H A-1003 Cl Cl OCH₃ CF₃ H A-1004 Cl Cl —O(CH₂)₂O— H A-1005 Cl Cl —OCH₂CH₂—^(#) H A-1006 Cl Cl —CH═CH—CH═CH— H A-1007 Cl Cl F H F A-1008 Cl Cl Cl H F A-1009 Cl Cl CH₃ H F A-1010 Cl Cl CF₃ H F A-1011 Cl Cl OCH₃ H F A-1012 Cl Cl F F F A-1013 Cl Cl Cl F F A-1014 Cl Cl CH₃ F F A-1015 Cl Cl CF₃ F F A-1016 Cl Cl OCH₃ F F A-1017 Cl Cl F Cl F A-1018 Cl Cl Cl Cl F A-1019 Cl Cl CH₃ Cl F A-1020 Cl Cl CF₃ Cl F A-1021 Cl Cl OCH₃ Cl F A-1022 Cl Cl F CH₃ F A-1023 Cl Cl Cl CH₃ F A-1024 Cl Cl CH₃ CH₃ F A-1025 Cl Cl CF₃ CH₃ F A-1026 Cl Cl OCH₃ CH₃ F A-1027 Cl Cl F CF₃ F A-1028 Cl Cl Cl CF₃ F A-1029 Cl Cl CH₃ CF₃ F A-1030 Cl Cl CF₃ CF₃ F A-1031 Cl Cl OCH₃ CF₃ F A-1032 Cl Cl —O(CH₂)₂O— F A-1033 Cl Cl —OCH₂CH₂—^(#) F A-1034 Cl Cl —CH═CH—CH═CH— F A-1035 Cl Cl F H Cl A-1036 Cl Cl Cl H Cl A-1037 Cl Cl CH₃ H Cl A-1038 Cl Cl CF₃ H Cl A-1039 Cl Cl OCH₃ H Cl A-1040 Cl Cl F F Cl A-1041 Cl Cl Cl F Cl A-1042 Cl Cl CH₃ F Cl A-1043 Cl Cl CF₃ F Cl A-1044 Cl Cl OCH₃ F Cl A-1045 Cl Cl F Cl Cl A-1046 Cl Cl Cl Cl Cl A-1047 Cl Cl CH₃ Cl Cl A-1048 Cl Cl CF₃ Cl Cl A-1049 Cl Cl OCH₃ Cl Cl A-1050 Cl Cl F CH₃ Cl A-1051 Cl Cl Cl CH₃ Cl A-1052 Cl Cl CH₃ CH₃ Cl A-1053 Cl Cl CF₃ CH₃ Cl A-1054 Cl Cl OCH₃ CH₃ Cl A-1055 Cl Cl F CF₃ Cl A-1056 Cl Cl Cl CF₃ Cl A-1057 Cl Cl CH₃ CF₃ Cl A-1058 Cl Cl CF₃ CF₃ Cl A-1059 Cl Cl OCH₃ CF₃ Cl A-1060 Cl Cl —O(CH₂)₂O— Cl A-1061 Cl Cl —OCH₂CH₂—^(#) Cl A-1062 Cl Cl —CH═CH—CH═CH— Cl A-1063 Cl Cl F H CH₃ A-1064 Cl Cl Cl H CH₃ A-1065 Cl Cl CH₃ H CH₃ A-1066 Cl Cl CF₃ H CH₃ A-1067 Cl Cl OCH₃ H CH₃ A-1068 Cl Cl F F CH₃ A-1069 Cl Cl Cl F CH₃ A-1070 Cl Cl CH₃ F CH₃ A-1071 Cl Cl CF₃ F CH₃ A-1072 Cl Cl OCH₃ F CH₃ A-1073 Cl Cl F Cl CH₃ A-1074 Cl Cl Cl Cl CH₃ A-1075 Cl Cl CH₃ Cl CH₃ A-1076 Cl Cl CF₃ Cl CH₃ A-1077 Cl Cl OCH₃ Cl CH₃ A-1078 Cl Cl F CH₃ CH₃ A-1079 Cl Cl Cl CH₃ CH₃ A-1080 Cl Cl CH₃ CH₃ CH₃ A-1081 Cl Cl CF₃ CH₃ CH₃ A-1082 Cl Cl OCH₃ CH₃ CH₃ A-1083 Cl Cl F CF₃ CH₃ A-1084 Cl Cl Cl CF₃ CH₃ A-1085 Cl Cl CH₃ CF₃ CH₃ A-1086 Cl Cl CF₃ CF₃ CH₃ A-1087 Cl Cl OCH₃ CF₃ CH₃ A-1088 Cl Cl —O(CH₂)₂O— CH₃ A-1089 Cl Cl —OCH₂CH₂—^(#) CH₃ A-1090 Cl Cl —CH═CH—CH═CH— CH₃ A-1091 Cl Cl F H CF₃ A-1092 Cl Cl Cl H CF₃ A-1093 Cl Cl CH₃ H CF₃ A-1094 Cl Cl CF₃ H CF₃ A-1095 Cl Cl OCH₃ H CF₃ A-1096 Cl Cl F F CF₃ A-1097 Cl Cl Cl F CF₃ A-1098 Cl Cl CH₃ F CF₃ A-1099 Cl Cl CF₃ F CF₃ A-1100 Cl Cl OCH₃ F CF₃ A-1101 Cl Cl F Cl CF₃ A-1102 Cl Cl Cl Cl CF₃ A-1103 Cl Cl CH₃ Cl CF₃ A-1104 Cl Cl CF₃ Cl CF₃ A-1105 Cl Cl OCH₃ Cl CF₃ A-1106 Cl Cl F CH₃ CF₃ A-1107 Cl Cl Cl CH₃ CF₃ A-1108 Cl Cl CH₃ CH₃ CF₃ A-1109 Cl Cl CF₃ CH₃ CF₃ A-1110 Cl Cl OCH₃ CH₃ CF₃ A-1111 Cl Cl F CF₃ CF₃ A-1112 Cl Cl Cl CF₃ CF₃ A-1113 Cl Cl CH₃ CF₃ CF₃ A-1114 Cl Cl CF₃ CF₃ CF₃ A-1115 Cl Cl OCH₃ CF₃ CF₃ A-1116 Cl Cl —O(CH₂)₂O— CF₃ A-1117 Cl Cl —OCH₂CH₂—^(#) CF₃ A-1118 Cl Cl —CH═CH—CH═CH— CF₃ A-1119 CH₃ Cl F H H A-1120 CH₃ Cl Cl H H A-1121 CH₃ Cl CH₃ H H A-1122 CH₃ Cl CF₃ H H A-1123 CH₃ Cl OCH₃ H H A-1124 CH₃ Cl F F H A-1125 CH₃ Cl Cl F H A-1126 CH₃ Cl CH₃ F H A-1127 CH₃ Cl CF₃ F H A-1128 CH₃ Cl OCH₃ F H A-1129 CH₃ Cl F Cl H A-1130 CH₃ Cl Cl Cl H A-1131 CH₃ Cl CH₃ Cl H A-1132 CH₃ Cl CF₃ Cl H A-1133 CH₃ Cl OCH₃ Cl H A-1134 CH₃ Cl F CH₃ H A-1135 CH₃ Cl Cl CH₃ H A-1136 CH₃ Cl CH₃ CH₃ H A-1137 CH₃ Cl CF₃ CH₃ H A-1138 CH₃ Cl OCH₃ CH₃ H A-1139 CH₃ Cl F CF₃ H A-1140 CH₃ Cl Cl CF₃ H A-1141 CH₃ Cl CH₃ CF₃ H A-1142 CH₃ Cl CF₃ CF₃ H A-1143 CH₃ Cl OCH₃ CF₃ H A-1144 CH₃ Cl —O(CH₂)₂O— H A-1145 CH₃ Cl —OCH₂CH₂—^(#) H A-1146 CH₃ Cl —CH═CH—CH═CH— H A-1147 CH₃ Cl F H F A-1148 CH₃ Cl Cl H F A-1149 CH₃ Cl CH₃ H F A-1150 CH₃ Cl CF₃ H F A-1151 CH₃ Cl OCH₃ H F A-1152 CH₃ Cl F F F A-1153 CH₃ Cl Cl F F A-1154 CH₃ Cl CH₃ F F A-1155 CH₃ Cl CF₃ F F A-1156 CH₃ Cl OCH₃ F F A-1157 CH₃ Cl F Cl F A-1158 CH₃ Cl Cl Cl F A-1159 CH₃ Cl CH₃ Cl F A-1160 CH₃ Cl CF₃ Cl F A-1161 CH₃ Cl OCH₃ Cl F A-1162 CH₃ Cl F CH₃ F A-1163 CH₃ Cl Cl CH₃ F A-1164 CH₃ Cl CH₃ CH₃ F A-1165 CH₃ Cl CF₃ CH₃ F A-1166 CH₃ Cl OCH₃ CH₃ F A-1167 CH₃ Cl F CF₃ F A-1168 CH₃ Cl Cl CF₃ F A-1169 CH₃ Cl CH₃ CF₃ F A-1170 CH₃ Cl CF₃ CF₃ F A-1171 CH₃ Cl OCH₃ CF₃ F A-1172 CH₃ Cl —O(CH₂)₂O— F A-1173 CH₃ Cl —OCH₂CH₂—^(#) F A-1174 CH₃ Cl —CH═CH—CH═CH— F A-1175 CH₃ Cl F H Cl A-1176 CH₃ Cl Cl H Cl A-1177 CH₃ Cl CH₃ H Cl A-1178 CH₃ Cl CF₃ H Cl A-1179 CH₃ Cl OCH₃ H Cl A-1180 CH₃ Cl F F Cl A-1181 CH₃ Cl Cl F Cl A-1182 CH₃ Cl CH₃ F Cl A-1183 CH₃ Cl CF₃ F Cl A-1184 CH₃ Cl OCH₃ F Cl A-1185 CH₃ Cl F Cl Cl A-1186 CH₃ Cl Cl Cl Cl A-1187 CH₃ Cl CH₃ Cl Cl A-1188 CH₃ Cl CF₃ Cl Cl A-1189 CH₃ Cl OCH₃ Cl Cl A-1190 CH₃ Cl F CH₃ Cl A-1191 CH₃ Cl Cl CH₃ Cl A-1192 CH₃ Cl CH₃ CH₃ Cl A-1193 CH₃ Cl CF₃ CH₃ Cl A-1194 CH₃ Cl OCH₃ CH₃ Cl A-1195 CH₃ Cl F CF₃ Cl A-1196 CH₃ Cl Cl CF₃ Cl A-1197 CH₃ Cl CH₃ CF₃ Cl A-1198 CH₃ Cl CF₃ CF₃ Cl A-1199 CH₃ Cl OCH₃ CF₃ Cl A-1200 CH₃ Cl —O(CH₂)₂O— Cl A-1201 CH₃ Cl —OCH₂CH₂—^(#) Cl A-1202 CH₃ Cl —CH═CH—CH═CH— Cl A-1203 CH₃ Cl F H CH₃ A-1204 CH₃ Cl Cl H CH₃ A-1205 CH₃ Cl CH₃ H CH₃ A-1206 CH₃ Cl CF₃ H CH₃ A-1207 CH₃ Cl OCH₃ H CH₃ A-1208 CH₃ Cl F F CH₃ A-1209 CH₃ Cl Cl F CH₃ A-1210 CH₃ Cl CH₃ F CH₃ A-1211 CH₃ Cl CF₃ F CH₃ A-1212 CH₃ Cl OCH₃ F CH₃ A-1213 CH₃ Cl F Cl CH₃ A-1214 CH₃ Cl Cl Cl CH₃ A-1215 CH₃ Cl CH₃ Cl CH₃ A-1216 CH₃ Cl CF₃ Cl CH₃ A-1217 CH₃ Cl OCH₃ Cl CH₃ A-1218 CH₃ Cl F CH₃ CH₃ A-1219 CH₃ Cl Cl CH₃ CH₃ A-1220 CH₃ Cl CH₃ CH₃ CH₃ A-1221 CH₃ Cl CF₃ CH₃ CH₃ A-1222 CH₃ Cl OCH₃ CH₃ CH₃ A-1223 CH₃ Cl F CF₃ CH₃ A-1224 CH₃ Cl Cl CF₃ CH₃ A-1225 CH₃ Cl CH₃ CF₃ CH₃ A-1226 CH₃ Cl CF₃ CF₃ CH₃ A-1227 CH₃ Cl OCH₃ CF₃ CH₃ A-1228 CH₃ Cl —O(CH₂)₂O— CH₃ A-1229 CH₃ Cl —OCH₂CH₂—^(#) CH₃ A-1230 CH₃ Cl —CH═CH—CH═CH— CH₃ A-1231 CH₃ Cl F H CF₃ A-1232 CH₃ Cl Cl H CF₃ A-1233 CH₃ Cl CH₃ H CF₃ A-1234 CH₃ Cl CF₃ H CF₃ A-1235 CH₃ Cl OCH₃ H CF₃ A-1236 CH₃ Cl F F CF₃ A-1237 CH₃ Cl Cl F CF₃ A-1238 CH₃ Cl CH₃ F CF₃ A-1239 CH₃ Cl CF₃ F CF₃ A-1240 CH₃ Cl OCH₃ F CF₃ A-1241 CH₃ Cl F Cl CF₃ A-1242 CH₃ Cl Cl Cl CF₃ A-1243 CH₃ Cl CH₃ Cl CF₃ A-1244 CH₃ Cl CF₃ Cl CF₃ A-1245 CH₃ Cl OCH₃ Cl CF₃ A-1246 CH₃ Cl F CH₃ CF₃ A-1247 CH₃ Cl Cl CH₃ CF₃ A-1248 CH₃ Cl CH₃ CH₃ CF₃ A-1249 CH₃ Cl CF₃ CH₃ CF₃ A-1250 CH₃ Cl OCH₃ CH₃ CF₃ A-1251 CH₃ Cl F CF₃ CF₃ A-1252 CH₃ Cl Cl CF₃ CF₃ A-1253 CH₃ Cl CH₃ CF₃ CF₃ A-1254 CH₃ Cl CF₃ CF₃ CF₃ A-1255 CH₃ Cl OCH₃ CF₃ CF₃ A-1256 CH₃ Cl —O(CH₂)₂O— CF₃ A-1257 CH₃ Cl —OCH₂CH₂—^(#) CF₃ A-1258 CH₃ Cl —CH═CH—CH═CH— CF₃ A-1259 CF₃ Cl F H H A-1260 CF₃ Cl Cl H H A-1261 CF₃ Cl CH₃ H H A-1262 CF₃ Cl CF₃ H H A-1263 CF₃ Cl OCH₃ H H A-1264 CF₃ Cl F F H A-1265 CF₃ Cl Cl F H A-1266 CF₃ Cl CH₃ F H A-1267 CF₃ Cl CF₃ F H A-1268 CF₃ Cl OCH₃ F H A-1269 CF₃ Cl F Cl H A-1270 CF₃ Cl Cl Cl H A-1271 CF₃ Cl CH₃ Cl H A-1272 CF₃ Cl CF₃ Cl H A-1273 CF₃ Cl OCH₃ Cl H A-1274 CF₃ Cl F CH₃ H A-1275 CF₃ Cl Cl CH₃ H A-1276 CF₃ Cl CH₃ CH₃ H A-1277 CF₃ Cl CF₃ CH₃ H A-1278 CF₃ Cl OCH₃ CH₃ H A-1279 CF₃ Cl F CF₃ H A-1280 CF₃ Cl Cl CF₃ H A-1281 CF₃ Cl CH₃ CF₃ H A-1282 CF₃ Cl CF₃ CF₃ H A-1283 CF₃ Cl OCH₃ CF₃ H A-1284 CF₃ Cl —O(CH₂)₂O— H A-1285 CF₃ Cl —OCH₂CH₂—^(#) H A-1286 CF₃ Cl —CH═CH—CH═CH— H A-1287 CF₃ Cl F H F A-1288 CF₃ Cl Cl H F A-1289 CF₃ Cl CH₃ H F A-1290 CF₃ Cl CF₃ H F A-1291 CF₃ Cl OCH₃ H F A-1292 CF₃ Cl F F F A-1293 CF₃ Cl Cl F F A-1294 CF₃ Cl CH₃ F F A-1295 CF₃ Cl CF₃ F F A-1296 CF₃ Cl OCH₃ F F A-1297 CF₃ Cl F Cl F A-1298 CF₃ Cl Cl Cl F A-1299 CF₃ Cl CH₃ Cl F A-1300 CF₃ Cl CF₃ Cl F A-1301 CF₃ Cl OCH₃ Cl F A-1302 CF₃ Cl F CH₃ F A-1303 CF₃ Cl Cl CH₃ F A-1304 CF₃ Cl CH₃ CH₃ F A-1305 CF₃ Cl CF₃ CH₃ F A-1306 CF₃ Cl OCH₃ CH₃ F A-1307 CF₃ Cl F CF₃ F A-1308 CF₃ Cl Cl CF₃ F A-1309 CF₃ Cl CH₃ CF₃ F A-1310 CF₃ Cl CF₃ CF₃ F A-1311 CF₃ Cl OCH₃ CF₃ F A-1312 CF₃ Cl —O(CH₂)₂O— F A-1313 CF₃ Cl —OCH₂CH₂—^(#) F A-1314 CF₃ Cl —CH═CH—CH═CH— F A-1315 CF₃ Cl F H Cl A-1316 CF₃ Cl Cl H Cl A-1317 CF₃ Cl CH₃ H Cl A-1318 CF₃ Cl CF₃ H Cl A-1319 CF₃ Cl OCH₃ H Cl A-1320 CF₃ Cl F F Cl A-1321 CF₃ Cl Cl F Cl A-1322 CF₃ Cl CH₃ F Cl A-1323 CF₃ Cl CF₃ F Cl A-1324 CF₃ Cl OCH₃ F Cl A-1325 CF₃ Cl F Cl Cl A-1326 CF₃ Cl Cl Cl Cl A-1327 CF₃ Cl CH₃ Cl Cl A-1328 CF₃ Cl CF₃ Cl Cl A-1329 CF₃ Cl OCH₃ Cl Cl A-1330 CF₃ Cl F CH₃ Cl A-1331 CF₃ Cl Cl CH₃ Cl A-1332 CF₃ Cl CH₃ CH₃ Cl A-1333 CF₃ Cl CF₃ CH₃ Cl A-1334 CF₃ Cl OCH₃ CH₃ Cl A-1335 CF₃ Cl F CF₃ Cl A-1336 CF₃ Cl Cl CF₃ Cl A-1337 CF₃ Cl CH₃ CF₃ Cl A-1338 CF₃ Cl CF₃ CF₃ Cl A-1339 CF₃ Cl OCH₃ CF₃ Cl A-1340 CF₃ Cl —O(CH₂)₂O— Cl A-1341 CF₃ Cl —OCH₂CH₂—^(#) Cl A-1342 CF₃ Cl —CH═CH—CH═CH— Cl A-1343 CF₃ Cl F H CH₃ A-1344 CF₃ Cl Cl H CH₃ A-1345 CF₃ Cl CH₃ H CH₃ A-1346 CF₃ Cl CF₃ H CH₃ A-1347 CF₃ Cl OCH₃ H CH₃ A-1348 CF₃ Cl F F CH₃ A-1349 CF₃ Cl Cl F CH₃ A-1350 CF₃ Cl CH₃ F CH₃ A-1351 CF₃ Cl CF₃ F CH₃ A-1352 CF₃ Cl OCH₃ F CH₃ A-1353 CF₃ Cl F Cl CH₃ A-1354 CF₃ Cl Cl Cl CH₃ A-1355 CF₃ Cl CH₃ Cl CH₃ A-1356 CF₃ Cl CF₃ Cl CH₃ A-1357 CF₃ Cl OCH₃ Cl CH₃ A-1358 CF₃ Cl F CH₃ CH₃ A-1359 CF₃ Cl Cl CH₃ CH₃ A-1360 CF₃ Cl CH₃ CH₃ CH₃ A-1361 CF₃ Cl CF₃ CH₃ CH₃ A-1362 CF₃ Cl OCH₃ CH₃ CH₃ A-1363 CF₃ Cl F CF₃ CH₃ A-1364 CF₃ Cl Cl CF₃ CH₃ A-1365 CF₃ Cl CH₃ CF₃ CH₃ A-1366 CF₃ Cl CF₃ CF₃ CH₃ A-1367 CF₃ Cl OCH₃ CF₃ CH₃ A-1368 CF₃ Cl —O(CH₂)₂O— CH₃ A-1369 CF₃ Cl —OCH₂CH₂—^(#) CH₃ A-1370 CF₃ Cl —CH═CH—CH═CH— CH₃ A-1371 CF₃ Cl F H CF₃ A-1372 CF₃ Cl Cl H CF₃ A-1373 CF₃ Cl CH₃ H CF₃ A-1374 CF₃ Cl CF₃ H CF₃ A-1375 CF₃ Cl OCH₃ H CF₃ A-1376 CF₃ Cl F F CF₃ A-1377 CF₃ Cl Cl F CF₃ A-1378 CF₃ Cl CH₃ F CF₃ A-1379 CF₃ Cl CF₃ F CF₃ A-1380 CF₃ Cl OCH₃ F CF₃ A-1381 CF₃ Cl F Cl CF₃ A-1382 CF₃ Cl Cl Cl CF₃ A-1383 CF₃ Cl CH₃ Cl CF₃ A-1384 CF₃ Cl CF₃ Cl CF₃ A-1385 CF₃ Cl OCH₃ Cl CF₃ A-1386 CF₃ Cl F CH₃ CF₃ A-1387 CF₃ Cl Cl CH₃ CF₃ A-1388 CF₃ Cl CH₃ CH₃ CF₃ A-1389 CF₃ Cl CF₃ CH₃ CF₃ A-1390 CF₃ Cl OCH₃ CH₃ CF₃ A-1391 CF₃ Cl F CF₃ CF₃ A-1392 CF₃ Cl Cl CF₃ CF₃ A-1393 CF₃ Cl CH₃ CF₃ CF₃ A-1394 CF₃ Cl CF₃ CF₃ CF₃ A-1395 CF₃ Cl OCH₃ CF₃ CF₃ A-1396 CF₃ Cl —O(CH₂)₂O— CF₃ A-1397 CF₃ Cl —OCH₂CH₂—^(#) CF₃ A-1398 CF₃ Cl —CH═CH—CH═CH— CF₃ A-1399 H CH₃ F H H A-1400 H CH₃ Cl H H A-1401 H CH₃ CH₃ H H A-1402 H CH₃ CF₃ H H A-1403 H CH₃ OCH₃ H H A-1404 H CH₃ F F H A-1405 H CH₃ Cl F H A-1406 H CH₃ CH₃ F H A-1407 H CH₃ CF₃ F H A-1408 H CH₃ OCH₃ F H A-1409 H CH₃ F Cl H A-1410 H CH₃ Cl Cl H A-1411 H CH₃ CH₃ Cl H A-1412 H CH₃ CF₃ Cl H A-1413 H CH₃ OCH₃ Cl H A-1414 H CH₃ F CH₃ H A-1415 H CH₃ Cl CH₃ H A-1416 H CH₃ CH₃ CH₃ H A-1417 H CH₃ CF₃ CH₃ H A-1418 H CH₃ OCH₃ CH₃ H A-1419 H CH₃ F CF₃ H A-1420 H CH₃ Cl CF₃ H A-1421 H CH₃ CH₃ CF₃ H A-1422 H CH₃ CF₃ CF₃ H A-1423 H CH₃ OCH₃ CF₃ H A-1424 H CH₃ —O(CH₂)₂O— H A-1425 H CH₃ —OCH₂CH₂—^(#) H₃ A-1426 H CH₃ —CH═CH—CH═CH— H A-1427 H CH₃ F H F A-1428 H CH₃ Cl H F A-1429 H CH₃ CH₃ H F A-1430 H CH₃ CF₃ H F A-1431 H CH₃ OCH₃ H F A-1432 H CH₃ F F F A-1433 H CH₃ Cl F F A-1434 H CH₃ CH₃ F F A-1435 H CH₃ CF₃ F F A-1436 H CH₃ OCH₃ F F A-1437 H CH₃ F Cl F A-1438 H CH₃ Cl Cl F A-1439 H CH₃ CH₃ Cl F A-1440 H CH₃ CF₃ Cl F A-1441 H CH₃ OCH₃ Cl F A-1442 H CH₃ F CH₃ F A-1443 H CH₃ Cl CH₃ F A-1444 H CH₃ CH₃ CH₃ F A-1445 H CH₃ CF₃ CH₃ F A-1446 H CH₃ OCH₃ CH₃ F A-1447 H CH₃ F CF₃ F A-1448 H CH₃ Cl CF₃ F A-1449 H CH₃ CH₃ CF₃ F A-1450 H CH₃ CF₃ CF₃ F A-1451 H CH₃ OCH₃ CF₃ F A-1452 H CH₃ —O(CH₂)₂O— F A-1453 H CH₃ —OCH₂CH₂—^(#) F A-1454 H CH₃ —CH═CH—CH═CH— F A-1455 H CH₃ F H Cl A-1456 H CH₃ Cl H Cl A-1457 H CH₃ CH₃ H Cl A-1458 H CH₃ CF₃ H Cl A-1459 H CH₃ OCH₃ H Cl A-1460 H CH₃ F F Cl A-1461 H CH₃ Cl F Cl A-1462 H CH₃ CH₃ F Cl A-1463 H CH₃ CF₃ F Cl A-1464 H CH₃ OCH₃ F Cl A-1465 H CH₃ F Cl Cl A-1466 H CH₃ Cl Cl Cl A-1467 H CH₃ CH₃ Cl Cl A-1468 H CH₃ CF₃ Cl Cl A-1469 H CH₃ OCH₃ Cl Cl A-1470 H CH₃ F CH₃ Cl A-1471 H CH₃ Cl CH₃ Cl A-1472 H CH₃ CH₃ CH₃ Cl A-1473 H CH₃ CF₃ CH₃ Cl A-1474 H CH₃ OCH₃ CH₃ Cl A-1475 H CH₃ F CF₃ Cl A-1476 H CH₃ Cl CF₃ Cl A-1477 H CH₃ CH₃ CF₃ Cl A-1478 H CH₃ CF₃ CF₃ Cl A-1479 H CH₃ OCH₃ CF₃ Cl A-1480 H CH₃ —O(CH₂)₂O— Cl A-1481 H CH₃ —OCH₂CH₂—^(#) Cl A-1482 H CH₃ —CH═CH—CH═CH— Cl A-1483 H CH₃ F H CH₃ A-1484 H CH₃ Cl H CH₃ A-1485 H CH₃ CH₃ H CH₃ A-1486 H CH₃ CF₃ H CH₃ A-1487 H CH₃ OCH₃ H CH₃ A-1488 H CH₃ F F CH₃ A-1489 H CH₃ Cl F CH₃ A-1490 H CH₃ CH₃ F CH₃ A-1491 H CH₃ CF₃ F CH₃ A-1492 H CH₃ OCH₃ F CH₃ A-1493 H CH₃ F Cl CH₃ A-1494 H CH₃ Cl Cl CH₃ A-1495 H CH₃ CH₃ Cl CH₃ A-1496 H CH₃ CF₃ Cl CH₃ A-1497 H CH₃ OCH₃ Cl CH₃ A-1498 H CH₃ F CH₃ CH₃ A-1499 H CH₃ Cl CH₃ CH₃ A-1500 H CH₃ CH₃ CH₃ CH₃ A-1501 H CH₃ CF₃ CH₃ CH₃ A-1502 H CH₃ OCH₃ CH₃ CH₃ A-1503 H CH₃ F CF₃ CH₃ A-1504 H CH₃ Cl CF₃ CH₃ A-1505 H CH₃ CH₃ CF₃ CH₃ A-1506 H CH₃ CF₃ CF₃ CH₃ A-1507 H CH₃ OCH₃ CF₃ CH₃ A-1508 H CH₃ —O(CH₂)₂O— CH₃ A-1509 H CH₃ —OCH₂CH₂—^(#) CH₃ A-1510 H CH₃ —CH═CH—CH═CH— CH₃ A-1511 H CH₃ F H CF₃ A-1512 H CH₃ Cl H CF₃ A-1513 H CH₃ CH₃ H CF₃ A-1514 H CH₃ CF₃ H CF₃ A-1515 H CH₃ OCH₃ H CF₃ A-1516 H CH₃ F F CF₃ A-1517 H CH₃ Cl F CF₃ A-1518 H CH₃ CH₃ F CF₃ A-1519 H CH₃ CF₃ F CF₃ A-1520 H CH₃ OCH₃ F CF₃ A-1521 H CH₃ F Cl CF₃ A-1522 H CH₃ Cl Cl CF₃ A-1523 H CH₃ CH₃ Cl CF₃ A-1524 H CH₃ CF₃ Cl CF₃ A-1525 H CH₃ OCH₃ Cl CF₃ A-1526 H CH₃ F CH₃ CF₃ A-1527 H CH₃ Cl CH₃ CF₃ A-1528 H CH₃ CH₃ CH₃ CF₃ A-1529 H CH₃ CF₃ CH₃ CF₃ A-1530 H CH₃ OCH₃ CH₃ CF₃ A-1531 H CH₃ F CF₃ CF₃ A-1532 H CH₃ Cl CF₃ CF₃ A-1533 H CH₃ CH₃ CF₃ CF₃ A-1534 H CH₃ CF₃ CF₃ CF₃ A-1535 H CH₃ OCH₃ CF₃ CF₃ A-1536 H CH₃ —O(CH₂)₂O— CF₃ A-1537 H CH₃ —OCH₂CH₂—^(#) CF₃ A-1538 H CH₃ —CH═CH—CH═CH— CF₃ A-1539 F CH₃ F H H A-1540 F CH₃ Cl H H A-1541 F CH₃ CH₃ H H A-1542 F CH₃ CF₃ H H A-1543 F CH₃ OCH₃ H H A-1544 F CH₃ F F H A-1545 F CH₃ Cl F H A-1546 F CH₃ CH₃ F H A-1547 F CH₃ CF₃ F H A-1548 F CH₃ OCH₃ F H A-1549 F CH₃ F Cl H A-1550 F CH₃ Cl Cl H A-1551 F CH₃ CH₃ Cl H A-1552 F CH₃ CF₃ Cl H A-1553 F CH₃ OCH₃ Cl H A-1554 F CH₃ F CH₃ H A-1555 F CH₃ Cl CH₃ H A-1556 F CH₃ CH₃ CH₃ H A-1557 F CH₃ CF₃ CH₃ H A-1558 F CH₃ OCH₃ CH₃ H A-1559 F CH₃ F CF₃ H A-1560 F CH₃ Cl CF₃ H A-1561 F CH₃ CH₃ CF₃ H A-1562 F CH₃ CF₃ CF₃ H A-1563 F CH₃ OCH₃ CF₃ H A-1564 F CH₃ —O(CH₂)₂O— H A-1565 F CH₃ —OCH₂CH₂—^(#) H A-1566 F CH₃ —CH═CH—CH═CH— H A-1567 F CH₃ F H F A-1568 F CH₃ Cl H F A-1569 F CH₃ CH₃ H F A-1570 F CH₃ CF₃ H F A-1571 F CH₃ OCH₃ H F A-1572 F CH₃ F F F A-1573 F CH₃ Cl F F A-1574 F CH₃ CH₃ F F A-1575 F CH₃ CF₃ F F A-1576 F CH₃ OCH₃ F F A-1577 F CH₃ F Cl F A-1578 F CH₃ Cl Cl F A-1579 F CH₃ CH₃ Cl F A-1580 F CH₃ CF₃ Cl F A-1581 F CH₃ OCH₃ Cl F A-1582 F CH₃ F CH₃ F A-1583 F CH₃ Cl CH₃ F A-1584 F CH₃ CH₃ CH₃ F A-1585 F CH₃ CF₃ CH₃ F A-1586 F CH₃ OCH₃ CH₃ F A-1587 F CH₃ F CF₃ F A-1588 F CH₃ Cl CF₃ F A-1589 F CH₃ CH₃ CF₃ F A-1590 F CH₃ CF₃ CF₃ F A-1591 F CH₃ OCH₃ CF₃ F A-1592 F CH₃ —O(CH₂)₂O— F A-1593 F CH₃ —OCH₂CH₂—^(#) F A-1594 F CH₃ —CH═CH—CH═CH— F A-1595 F CH₃ F H Cl A-1596 F CH₃ Cl H Cl A-1597 F CH₃ CH₃ H Cl A-1598 F CH₃ CF₃ H Cl A-1599 F CH₃ OCH₃ H Cl A-1600 F CH₃ F F Cl A-1601 F CH₃ Cl F Cl A-1602 F CH₃ CH₃ F Cl A-1603 F CH₃ CF₃ F Cl A-1604 F CH₃ OCH₃ F Cl A-1605 F CH₃ F Cl Cl A-1606 F CH₃ Cl Cl Cl A-1607 F CH₃ CH₃ Cl Cl A-1608 F CH₃ CF₃ Cl Cl A-1609 F CH₃ OCH₃ Cl Cl A-1610 F CH₃ F CH₃ Cl A-1611 F CH₃ Cl CH₃ Cl A-1612 F CH₃ CH₃ CH₃ Cl A-1613 F CH₃ CF₃ CH₃ Cl A-1614 F CH₃ OCH₃ CH₃ Cl A-1615 F CH₃ F CF₃ Cl A-1616 F CH₃ Cl CF₃ Cl A-1617 F CH₃ CH₃ CF₃ Cl A-1618 F CH₃ CF₃ CF₃ Cl A-1619 F CH₃ OCH₃ CF₃ Cl A-1620 F CH₃ —O(CH₂)₂O— Cl A-1621 F CH₃ —OCH₂CH₂—^(#) Cl A-1622 F CH₃ —CH═CH—CH═CH— Cl A-1623 F CH₃ F H CH₃ A-1624 F CH₃ Cl H CH₃ A-1625 F CH₃ CH₃ H CH₃ A-1626 F CH₃ CF₃ H CH₃ A-1627 F CH₃ OCH₃ H CH₃ A-1628 F CH₃ F F CH₃ A-1629 F CH₃ Cl F CH₃ A-1630 F CH₃ CH₃ F CH₃ A-1631 F CH₃ CF₃ F CH₃ A-1632 F CH₃ OCH₃ F CH₃ A-1633 F CH₃ F Cl CH₃ A-1634 F CH₃ Cl Cl CH₃ A-1635 F CH₃ CH₃ Cl CH₃ A-1636 F CH₃ CF₃ Cl CH₃ A-1637 F CH₃ OCH₃ Cl CH₃ A-1638 F CH₃ F CH₃ CH₃ A-1639 F CH₃ Cl CH₃ CH₃ A-1640 F CH₃ CH₃ CH₃ CH₃ A-1641 F CH₃ CF₃ CH₃ CH₃ A-1642 F CH₃ OCH₃ CH₃ CH₃ A-1643 F CH₃ F CF₃ CH₃ A-1644 F CH₃ Cl CF₃ CH₃ A-1645 F CH₃ CH₃ CF₃ CH₃ A-1646 F CH₃ CF₃ CF₃ CH₃ A-1647 F CH₃ OCH₃ CF₃ CH₃ A-1648 F CH₃ —O(CH₂)₂O— CH₃ A-1649 F CH₃ —OCH₂CH₂—^(#) CH₃ A-1650 F CH₃ —CH═CH—CH═CH— CH₃ A-1651 F CH₃ F H CF₃ A-1652 F CH₃ Cl H CF₃ A-1653 F CH₃ CH₃ H CF₃ A-1654 F CH₃ CF₃ H CF₃ A-1655 F CH₃ OCH₃ H CF₃ A-1656 F CH₃ F F CF₃ A-1657 F CH₃ Cl F CF₃ A-1658 F CH₃ CH₃ F CF₃ A-1659 F CH₃ CF₃ F CF₃ A-1660 F CH₃ OCH₃ F CF₃ A-1661 F CH₃ F Cl CF₃ A-1662 F CH₃ Cl Cl CF₃ A-1663 F CH₃ CH₃ Cl CF₃ A-1664 F CH₃ CF₃ Cl CF₃ A-1665 F CH₃ OCH₃ Cl CF₃ A-1666 F CH₃ F CH₃ CF₃ A-1667 F CH₃ Cl CH₃ CF₃ A-1668 F CH₃ CH₃ CH₃ CF₃ A-1669 F CH₃ CF₃ CH₃ CF₃ A-1670 F CH₃ OCH₃ CH₃ CF₃ A-1671 F CH₃ F CF₃ CF₃ A-1672 F CH₃ Cl CF₃ CF₃ A-1673 F CH₃ CH₃ CF₃ CF₃ A-1674 F CH₃ CF₃ CF₃ CF₃ A-1675 F CH₃ OCH₃ CF₃ CF₃ A-1676 F CH₃ —O(CH₂)₂O— CF₃ A-1677 F CH₃ —OCH₂CH₂—^(#) CF₃ A-1678 F CH₃ —CH═CH—CH═CH— CF₃ A-1679 Cl CH₃ F H H A-1680 Cl CH₃ Cl H H A-1681 Cl CH₃ CH₃ H H A-1682 Cl CH₃ CF₃ H H A-1683 Cl CH₃ OCH₃ H H A-1684 Cl CH₃ F F H A-1685 Cl CH₃ Cl F H A-1686 Cl CH₃ CH₃ F H A-1687 Cl CH₃ CF₃ F H A-1688 Cl CH₃ OCH₃ F H A-1689 Cl CH₃ F Cl H A-1690 Cl CH₃ Cl Cl H A-1691 Cl CH₃ CH₃ Cl H A-1692 Cl CH₃ CF₃ Cl H A-1693 Cl CH₃ OCH₃ Cl H A-1694 Cl CH₃ F CH₃ H A-1695 Cl CH₃ Cl CH₃ H A-1696 Cl CH₃ CH₃ CH₃ H A-1697 Cl CH₃ CF₃ CH₃ H A-1698 Cl CH₃ OCH₃ CH₃ H A-1699 Cl CH₃ F CF₃ H A-1700 Cl CH₃ Cl CF₃ H A-1701 Cl CH₃ CH₃ CF₃ H A-1702 Cl CH₃ CF₃ CF₃ H A-1703 Cl CH₃ OCH₃ CF₃ H A-1704 Cl CH₃ —O(CH₂)₂O— H A-1705 Cl CH₃ —OCH₂CH₂—^(#) H A-1706 Cl CH₃ —CH═CH—CH═CH— H A-1707 Cl CH₃ F H F A-1708 Cl CH₃ Cl H F A-1709 Cl CH₃ CH₃ H F A-1710 Cl CH₃ CF₃ H F A-1711 Cl CH₃ OCH₃ H F A-1712 Cl CH₃ F F F A-1713 Cl CH₃ Cl F F A-1714 Cl CH₃ CH₃ F F A-1715 Cl CH₃ CF₃ F F A-1716 Cl CH₃ OCH₃ F F A-1717 Cl CH₃ F Cl F A-1718 Cl CH₃ Cl Cl F A-1719 Cl CH₃ CH₃ Cl F A-1720 Cl CH₃ CF₃ Cl F A-1721 Cl CH₃ OCH₃ Cl F A-1722 Cl CH₃ F CH₃ F A-1723 Cl CH₃ Cl CH₃ F A-1724 Cl CH₃ CH₃ CH₃ F A-1725 Cl CH₃ CF₃ CH₃ F A-1726 Cl CH₃ OCH₃ CH₃ F A-1727 Cl CH₃ F CF₃ F A-1728 Cl CH₃ Cl CF₃ F A-1729 Cl CH₃ CH₃ CF₃ F A-1730 Cl CH₃ CF₃ CF₃ F A-1731 Cl CH₃ OCH₃ CF₃ F A-1732 Cl CH₃ —O(CH₂)₂O— F A-1733 Cl CH₃ —OCH₂CH₂—^(#) F A-1734 Cl CH₃ —CH═CH—CH═CH— F₃ A-1735 Cl CH₃ F H Cl A-1736 Cl CH₃ Cl H Cl A-1737 Cl CH₃ CH₃ H Cl A-1738 Cl CH₃ CF₃ H Cl A-1739 Cl CH₃ OCH₃ H Cl A-1740 Cl CH₃ F F Cl A-1741 Cl CH₃ Cl F Cl A-1742 Cl CH₃ CH₃ F Cl A-1743 Cl CH₃ CF₃ F Cl A-1744 Cl CH₃ OCH₃ F Cl A-1745 Cl CH₃ F Cl Cl A-1746 Cl CH₃ Cl Cl Cl A-1747 Cl CH₃ CH₃ Cl Cl A-1748 Cl CH₃ CF₃ Cl Cl A-1749 Cl CH₃ OCH₃ Cl Cl A-1750 Cl CH₃ F CH₃ Cl A-1751 Cl CH₃ Cl CH₃ Cl A-1752 Cl CH₃ CH₃ CH₃ Cl A-1753 Cl CH₃ CF₃ CH₃ Cl A-1754 Cl CH₃ OCH₃ CH₃ Cl A-1755 Cl CH₃ F CF₃ Cl A-1756 Cl CH₃ Cl CF₃ Cl A-1757 Cl CH₃ CH₃ CF₃ Cl A-1758 Cl CH₃ CF₃ CF₃ Cl A-1759 Cl CH₃ OCH₃ CF₃ Cl A-1760 Cl CH₃ —O(CH₂)₂O— Cl A-1761 Cl CH₃ —OCH₂CH₂—^(#) Cl A-1762 Cl CH₃ —CH═CH—CH═CH— Cl A-1763 Cl CH₃ F H CH₃ A-1764 Cl CH₃ Cl H CH₃ A-1765 Cl CH₃ CH₃ H CH₃ A-1766 Cl CH₃ CF₃ H CH₃ A-1767 Cl CH₃ OCH₃ H CH₃ A-1768 Cl CH₃ F F CH₃ A-1769 Cl CH₃ Cl F CH₃ A-1770 Cl CH₃ CH₃ F CH₃ A-1771 Cl CH₃ CF₃ F CH₃ A-1772 Cl CH₃ OCH₃ F CH₃ A-1773 Cl CH₃ F Cl CH₃ A-1774 Cl CH₃ Cl Cl CH₃ A-1775 Cl CH₃ CH₃ Cl CH₃ A-1776 Cl CH₃ CF₃ Cl CH₃ A-1777 Cl CH₃ OCH₃ Cl CH₃ A-1778 Cl CH₃ F CH₃ CH₃ A-1779 Cl CH₃ Cl CH₃ CH₃ A-1780 Cl CH₃ CH₃ CH₃ CH₃ A-1781 Cl CH₃ CF₃ CH₃ CH₃ A-1782 Cl CH₃ OCH₃ CH₃ CH₃ A-1783 Cl CH₃ F CF₃ CH₃ A-1784 Cl CH₃ Cl CF₃ CH₃ A-1785 Cl CH₃ CH₃ CF₃ CH₃ A-1786 Cl CH₃ CF₃ CF₃ CH₃ A-1787 Cl CH₃ OCH₃ CF₃ CH₃ A-1788 Cl CH₃ —O(CH₂)₂O— CH₃ A-1789 Cl CH₃ —OCH₂CH₂—^(#) CH₃ A-1790 Cl CH₃ —CH═CH—CH═CH— CH₃ A-1791 Cl CH₃ F H CF₃ A-1792 Cl CH₃ Cl H CF₃ A-1793 Cl CH₃ CH₃ H CF₃ A-1794 Cl CH₃ CF₃ H CF₃ A-1795 Cl CH₃ OCH₃ H CF₃ A-1796 Cl CH₃ F F CF₃ A-1797 Cl CH₃ Cl F CF₃ A-1798 Cl CH₃ CH₃ F CF₃ A-1799 Cl CH₃ CF₃ F CF₃ A-1800 Cl CH₃ OCH₃ F CF₃ A-1801 Cl CH₃ F Cl CF₃ A-1802 Cl CH₃ Cl Cl CF₃ A-1803 Cl CH₃ CH₃ Cl CF₃ A-1804 Cl CH₃ CF₃ Cl CF₃ A-1805 Cl CH₃ OCH₃ Cl CF₃ A-1806 Cl CH₃ F CH₃ CF₃ A-1807 Cl CH₃ Cl CH₃ CF₃ A-1808 Cl CH₃ CH₃ CH₃ CF₃ A-1809 Cl CH₃ CF₃ CH₃ CF₃ A-1810 Cl CH₃ OCH₃ CH₃ CF₃ A-1811 Cl CH₃ F CF₃ CF₃ A-1812 Cl CH₃ Cl CF₃ CF₃ A-1813 Cl CH₃ CH₃ CF₃ CF₃ A-1814 Cl CH₃ CF₃ CF₃ CF₃ A-1815 Cl CH₃ OCH₃ CF₃ CF₃ A-1816 Cl CH₃ —O(CH₂)₂O— CF₃ A-1817 Cl CH₃ —OCH₂CH₂—^(#) CF₃ A-1818 Cl CH₃ —CH═CH—CH═CH— CF₃ A-1819 CH₃ CH₃ F H H A-1820 CH₃ CH₃ Cl H H A-1821 CH₃ CH₃ CH₃ H H A-1822 CH₃ CH₃ CF₃ H H A-1823 CH₃ CH₃ OCH₃ H H A-1824 CH₃ CH₃ F F H A-1825 CH₃ CH₃ Cl F H A-1826 CH₃ CH₃ CH₃ F H A-1827 CH₃ CH₃ CF₃ F H A-1828 CH₃ CH₃ OCH₃ F H A-1829 CH₃ CH₃ F Cl H A-1830 CH₃ CH₃ Cl Cl H A-1831 CH₃ CH₃ CH₃ Cl H A-1832 CH₃ CH₃ CF₃ Cl H A-1833 CH₃ CH₃ OCH₃ Cl H A-1834 CH₃ CH₃ F CH₃ H A-1835 CH₃ CH₃ Cl CH₃ H A-1836 CH₃ CH₃ CH₃ CH₃ H A-1837 CH₃ CH₃ CF₃ CH₃ H A-1838 CH₃ CH₃ OCH₃ CH₃ H A-1839 CH₃ CH₃ F CF₃ H A-1840 CH₃ CH₃ Cl CF₃ H A-1841 CH₃ CH₃ CH₃ CF₃ H A-1842 CH₃ CH₃ CF₃ CF₃ H A-1843 CH₃ CH₃ OCH₃ CF₃ H A-1844 CH₃ CH₃ —O(CH₂)₂O— H A-1845 CH₃ CH₃ —OCH₂CH₂—^(#) H A-1846 CH₃ CH₃ —CH═CH—CH═CH— H A-1847 CH₃ CH₃ F H F A-1848 CH₃ CH₃ Cl H F A-1849 CH₃ CH₃ CH₃ H F A-1850 CH₃ CH₃ CF₃ H F A-1851 CH₃ CH₃ OCH₃ H F A-1852 CH₃ CH₃ F F F A-1853 CH₃ CH₃ Cl F F A-1854 CH₃ CH₃ CH₃ F F A-1855 CH₃ CH₃ CF₃ F F A-1856 CH₃ CH₃ OCH₃ F F A-1857 CH₃ CH₃ F Cl F A-1858 CH₃ CH₃ Cl Cl F A-1859 CH₃ CH₃ CH₃ Cl F A-1860 CH₃ CH₃ CF₃ Cl F A-1861 CH₃ CH₃ OCH₃ Cl F A-1862 CH₃ CH₃ F CH₃ F A-1863 CH₃ CH₃ Cl CH₃ F A-1864 CH₃ CH₃ CH₃ CH₃ F A-1865 CH₃ CH₃ CF₃ CH₃ F A-1866 CH₃ CH₃ OCH₃ CH₃ F A-1867 CH₃ CH₃ F CF₃ F A-1868 CH₃ CH₃ Cl CF₃ F A-1869 CH₃ CH₃ CH₃ CF₃ F A-1870 CH₃ CH₃ CF₃ CF₃ F A-1871 CH₃ CH₃ OCH₃ CF₃ F A-1872 CH₃ CH₃ —O(CH₂)₂O— F A-1873 CH₃ CH₃ —OCH₂CH₂—^(#) F A-1874 CH₃ CH₃ —CH═CH—CH═CH— F A-1875 CH₃ CH₃ F H Cl A-1876 CH₃ CH₃ Cl H Cl A-1877 CH₃ CH₃ CH₃ H Cl A-1878 CH₃ CH₃ CF₃ H Cl A-1879 CH₃ CH₃ OCH₃ H Cl A-1880 CH₃ CH₃ F F Cl A-1881 CH₃ CH₃ Cl F Cl A-1882 CH₃ CH₃ CH₃ F Cl A-1883 CH₃ CH₃ CF₃ F Cl A-1884 CH₃ CH₃ OCH₃ F Cl A-1885 CH₃ CH₃ F Cl Cl A-1886 CH₃ CH₃ Cl Cl Cl A-1887 CH₃ CH₃ CH₃ Cl Cl A-1888 CH₃ CH₃ CF₃ Cl Cl A-1889 CH₃ CH₃ OCH₃ Cl Cl A-1890 CH₃ CH₃ F CH₃ Cl A-1891 CH₃ CH₃ Cl CH₃ Cl A-1892 CH₃ CH₃ CH₃ CH₃ Cl A-1893 CH₃ CH₃ CF₃ CH₃ Cl A-1894 CH₃ CH₃ OCH₃ CH₃ Cl A-1895 CH₃ CH₃ F CF₃ Cl A-1896 CH₃ CH₃ Cl CF₃ Cl A-1897 CH₃ CH₃ CH₃ CF₃ Cl A-1898 CH₃ CH₃ CF₃ CF₃ Cl A-1899 CH₃ CH₃ OCH₃ CF₃ Cl A-1900 CH₃ CH₃ —O(CH₂)₂O— Cl A-1901 CH₃ CH₃ —OCH₂CH₂—^(#) Cl A-1902 CH₃ CH₃ —CH═CH—CH═CH— Cl A-1903 CH₃ CH₃ F H CH₃ A-1904 CH₃ CH₃ Cl H CH₃ A-1905 CH₃ CH₃ CH₃ H CH₃ A-1906 CH₃ CH₃ CF₃ H CH₃ A-1907 CH₃ CH₃ OCH₃ H CH₃ A-1908 CH₃ CH₃ F F CH₃ A-1909 CH₃ CH₃ Cl F CH₃ A-1910 CH₃ CH₃ CH₃ F CH₃ A-1911 CH₃ CH₃ CF₃ F CH₃ A-1912 CH₃ CH₃ OCH₃ F CH₃ A-1913 CH₃ CH₃ F Cl CH₃ A-1914 CH₃ CH₃ Cl Cl CH₃ A-1915 CH₃ CH₃ CH₃ Cl CH₃ A-1916 CH₃ CH₃ CF₃ Cl CH₃ A-1917 CH₃ CH₃ OCH₃ Cl CH₃ A-1918 CH₃ CH₃ F CH₃ CH₃ A-1919 CH₃ CH₃ Cl CH₃ CH₃ A-1920 CH₃ CH₃ CH₃ CH₃ CH₃ A-1921 CH₃ CH₃ CF₃ CH₃ CH₃ A-1922 CH₃ CH₃ OCH₃ CH₃ CH₃ A-1923 CH₃ CH₃ F CF₃ CH₃ A-1924 CH₃ CH₃ Cl CF₃ CH₃ A-1925 CH₃ CH₃ CH₃ CF₃ CH₃ A-1926 CH₃ CH₃ CF₃ CF₃ CH₃ A-1927 CH₃ CH₃ OCH₃ CF₃ CH₃ A-1928 CH₃ CH₃ —O(CH₂)₂O— CH₃ A-1929 CH₃ CH₃ —OCH₂CH₂—^(#) CH₃ A-1930 CH₃ CH₃ —CH═CH—CH═CH— CH₃ A-1931 CH₃ CH₃ F H CF₃ A-1932 CH₃ CH₃ Cl H CF₃ A-1933 CH₃ CH₃ CH₃ H CF₃ A-1934 CH₃ CH₃ CF₃ H CF₃ A-1935 CH₃ CH₃ OCH₃ H CF₃ A-1936 CH₃ CH₃ F F CF₃ A-1937 CH₃ CH₃ Cl F CF₃ A-1938 CH₃ CH₃ CH₃ F CF₃ A-1939 CH₃ CH₃ CF₃ F CF₃ A-1940 CH₃ CH₃ OCH₃ F CF₃ A-1941 CH₃ CH₃ F Cl CF₃ A-1942 CH₃ CH₃ Cl Cl CF₃ A-1943 CH₃ CH₃ CH₃ Cl CF₃ A-1944 CH₃ CH₃ CF₃ Cl CF₃ A-1945 CH₃ CH₃ OCH₃ Cl CF₃ A-1946 CH₃ CH₃ F CH₃ CF₃ A-1947 CH₃ CH₃ Cl CH₃ CF₃ A-1948 CH₃ CH₃ CH₃ CH₃ CF₃ A-1949 CH₃ CH₃ CF₃ CH₃ CF₃ A-1950 CH₃ CH₃ OCH₃ CH₃ CF₃ A-1951 CH₃ CH₃ F CF₃ CF₃ A-1952 CH₃ CH₃ Cl CF₃ CF₃ A-1953 CH₃ CH₃ CH₃ CF₃ CF₃ A-1954 CH₃ CH₃ CF₃ CF₃ CF₃ A-1955 CH₃ CH₃ OCH₃ CF₃ CF₃ A-1956 CH₃ CH₃ —O(CH₂)₂O— CF₃ A-1957 CH₃ CH₃ —OCH₂CH₂—^(#) CF₃ A-1958 CH₃ CH₃ —CH═CH—CH═CH— CF₃ A-1959 CF₃ CH₃ F H H A-1960 CF₃ CH₃ Cl H H A-1961 CF₃ CH₃ CH₃ H H A-1962 CF₃ CH₃ CF₃ H H A-1963 CF₃ CH₃ OCH₃ H H A-1964 CF₃ CH₃ F F H A-1965 CF₃ CH₃ Cl F H A-1966 CF₃ CH₃ CH₃ F H A-1967 CF₃ CH₃ CF₃ F H A-1968 CF₃ CH₃ OCH₃ F H A-1969 CF₃ CH₃ F Cl H A-1970 CF₃ CH₃ Cl Cl H A-1971 CF₃ CH₃ CH₃ Cl H A-1972 CF₃ CH₃ CF₃ Cl H A-1973 CF₃ CH₃ OCH₃ Cl H A-1974 CF₃ CH₃ F CH₃ H A-1975 CF₃ CH₃ Cl CH₃ H A-1976 CF₃ CH₃ CH₃ CH₃ H A-1977 CF₃ CH₃ CF₃ CH₃ H A-1978 CF₃ CH₃ OCH₃ CH₃ H A-1979 CF₃ CH₃ F CF₃ H A-1980 CF₃ CH₃ Cl CF₃ H A-1981 CF₃ CH₃ CH₃ CF₃ H A-1982 CF₃ CH₃ CF₃ CF₃ H A-1983 CF₃ CH₃ OCH₃ CF₃ H A-1984 CF₃ CH₃ —O(CH₂)₂O— H A-1985 CF₃ CH₃ —OCH₂CH₂—^(#) H A-1986 CF₃ CH₃ —CH═CH—CH═CH— H A-1987 CF₃ CH₃ F H F A-1988 CF₃ CH₃ Cl H F A-1989 CF₃ CH₃ CH₃ H F A-1990 CF₃ CH₃ CF₃ H F A-1991 CF₃ CH₃ OCH₃ H F A-1992 CF₃ CH₃ F F F A-1993 CF₃ CH₃ Cl F F A-1994 CF₃ CH₃ CH₃ F F A-1995 CF₃ CH₃ CF₃ F F A-1996 CF₃ CH₃ OCH₃ F F A-1997 CF₃ CH₃ F Cl F A-1998 CF₃ CH₃ Cl Cl F A-1999 CF₃ CH₃ CH₃ Cl F A-2000 CF₃ CH₃ CF₃ Cl F A-2001 CF₃ CH₃ OCH₃ Cl F A-2002 CF₃ CH₃ F CH₃ F A-2003 CF₃ CH₃ Cl CH₃ F A-2004 CF₃ CH₃ CH₃ CH₃ F A-2005 CF₃ CH₃ CF₃ CH₃ F A-2006 CF₃ CH₃ OCH₃ CH₃ F A-2007 CF₃ CH₃ F CF₃ F A-2008 CF₃ CH₃ Cl CF₃ F A-2009 CF₃ CH₃ CH₃ CF₃ F A-2010 CF₃ CH₃ CF₃ CF₃ F A-2011 CF₃ CH₃ OCH₃ CF₃ F A-2012 CF₃ CH₃ —O(CH₂)₂O— F A-2013 CF₃ CH₃ —OCH₂CH₂—^(#) F A-2014 CF₃ CH₃ —CH═CH—CH═CH— F A-2015 CF₃ CH₃ F H Cl A-2016 CF₃ CH₃ Cl H Cl A-2017 CF₃ CH₃ CH₃ H Cl A-2018 CF₃ CH₃ CF₃ H Cl A-2019 CF₃ CH₃ OCH₃ H Cl A-2020 CF₃ CH₃ F F Cl A-2021 CF₃ CH₃ Cl F Cl A-2022 CF₃ CH₃ CH₃ F Cl A-2023 CF₃ CH₃ CF₃ F Cl A-2024 CF₃ CH₃ OCH₃ F Cl A-2025 CF₃ CH₃ F Cl Cl A-2026 CF₃ CH₃ Cl Cl Cl A-2027 CF₃ CH₃ CH₃ Cl Cl A-2028 CF₃ CH₃ CF₃ Cl Cl A-2029 CF₃ CH₃ OCH₃ Cl Cl A-2030 CF₃ CH₃ F CH₃ Cl A-2031 CF₃ CH₃ Cl CH₃ Cl A-2032 CF₃ CH₃ CH₃ CH₃ Cl A-2033 CF₃ CH₃ CF₃ CH₃ Cl A-2034 CF₃ CH₃ OCH₃ CH₃ Cl A-2035 CF₃ CH₃ F CF₃ Cl A-2036 CF₃ CH₃ Cl CF₃ Cl A-2037 CF₃ CH₃ CH₃ CF₃ Cl A-2038 CF₃ CH₃ CF₃ CF₃ Cl A-2039 CF₃ CH₃ OCH₃ CF₃ Cl A-2040 CF₃ CH₃ —O(CH₂)₂O— Cl₃ A-2041 CF₃ CH₃ —OCH₂CH₂—^(#) Cl A-2042 CF₃ CH₃ —CH═CH—CH═CH— Cl A-2043 CF₃ CH₃ F H CH₃ A-2044 CF₃ CH₃ Cl H CH₃ A-2045 CF₃ CH₃ CH₃ H CH₃ A-2046 CF₃ CH₃ CF₃ H CH₃ A-2047 CF₃ CH₃ OCH₃ H CH₃ A-2048 CF₃ CH₃ F F CH₃ A-2049 CF₃ CH₃ Cl F CH₃ A-2050 CF₃ CH₃ CH₃ F CH₃ A-2051 CF₃ CH₃ CF₃ F CH₃ A-2052 CF₃ CH₃ OCH₃ F CH₃ A-2053 CF₃ CH₃ F Cl CH₃ A-2054 CF₃ CH₃ Cl Cl CH₃ A-2055 CF₃ CH₃ CH₃ Cl CH₃ A-2056 CF₃ CH₃ CF₃ Cl CH₃ A-2057 CF₃ CH₃ OCH₃ Cl CH₃ A-2058 CF₃ CH₃ F CH₃ CH₃ A-2059 CF₃ CH₃ Cl CH₃ CH₃ A-2060 CF₃ CH₃ CH₃ CH₃ CH₃ A-2061 CF₃ CH₃ CF₃ CH₃ CH₃ A-2062 CF₃ CH₃ OCH₃ CH₃ CH₃ A-2063 CF₃ CH₃ F CF₃ CH₃ A-2064 CF₃ CH₃ Cl CF₃ CH₃ A-2065 CF₃ CH₃ CH₃ CF₃ CH₃ A-2066 CF₃ CH₃ CF₃ CF₃ CH₃ A-2067 CF₃ CH₃ OCH₃ CF₃ CH₃ A-2068 CF₃ CH₃ —O(CH₂)₂O— CH₃ A-2069 CF₃ CH₃ —OCH₂CH₂—^(#) CH₃ A-2070 CF₃ CH₃ —CH═CH—CH═CH— CH₃ A-2071 CF₃ CH₃ F H CF₃ A-2072 CF₃ CH₃ Cl H CF₃ A-2073 CF₃ CH₃ CH₃ H CF₃ A-2074 CF₃ CH₃ CF₃ H CF₃ A-2075 CF₃ CH₃ OCH₃ H CF₃ A-2076 CF₃ CH₃ F F CF₃ A-2077 CF₃ CH₃ Cl F CF₃ A-2078 CF₃ CH₃ CH₃ F CF₃ A-2079 CF₃ CH₃ CF₃ F CF₃ A-2080 CF₃ CH₃ OCH₃ F CF₃ A-2081 CF₃ CH₃ F Cl CF₃ A-2082 CF₃ CH₃ Cl Cl CF₃ A-2083 CF₃ CH₃ CH₃ Cl CF₃ A-2084 CF₃ CH₃ CF₃ Cl CF₃ A-2085 CF₃ CH₃ OCH₃ Cl CF₃ A-2086 CF₃ CH₃ F CH₃ CF₃ A-2087 CF₃ CH₃ Cl CH₃ CF₃ A-2088 CF₃ CH₃ CH₃ CH₃ CF₃ A-2089 CF₃ CH₃ CF₃ CH₃ CF₃ A-2090 CF₃ CH₃ OCH₃ CH₃ CF₃ A-2091 CF₃ CH₃ F CF₃ CF₃ A-2092 CF₃ CH₃ Cl CF₃ CF₃ A-2093 CF₃ CH₃ CH₃ CF₃ CF₃ A-2094 CF₃ CH₃ CF₃ CF₃ CF₃ A-2095 CF₃ CH₃ OCH₃ CF₃ CF₃ A-2096 CF₃ CH₃ —O(CH₂)₂O— CF₃ A-2097 CF₃ CH₃ —OCH₂CH₂—^(#) CF₃ A-2098 CF₃ CH₃ —CH═CH—CH═CH— CF₃ A-2099 H CF₃ F H H A-2100 H CF₃ Cl H H A-2101 H CF₃ CH₃ H H A-2102 H CF₃ CF₃ H H A-2103 H CF₃ OCH₃ H H A-2104 H CF₃ F F H A-2105 H CF₃ Cl F H A-2106 H CF₃ CH₃ F H A-2107 H CF₃ CF₃ F H A-2108 H CF₃ OCH₃ F H A-2109 H CF₃ F Cl H A-2110 H CF₃ Cl Cl H A-2111 H CF₃ CH₃ Cl H A-2112 H CF₃ CF₃ Cl H A-2113 H CF₃ OCH₃ Cl H A-2114 H CF₃ F CH₃ H A-2115 H CF₃ Cl CH₃ H A-2116 H CF₃ CH₃ CH₃ H A-2117 H CF₃ CF₃ CH₃ H A-2118 H CF₃ OCH₃ CH₃ H A-2119 H CF₃ F CF₃ H A-2120 H CF₃ Cl CF₃ H A-2121 H CF₃ CH₃ CF₃ H A-2122 H CF₃ CF₃ CF₃ H A-2123 H CF₃ OCH₃ CF₃ H A-2124 H CF₃ —O(CH₂)₂O— H A-2125 H CF₃ —OCH₂CH₂—^(#) H A-2126 H CF₃ —CH═CH—CH═CH— H A-2127 H CF₃ F H F A-2128 H CF₃ Cl H F A-2129 H CF₃ CH₃ H F A-2130 H CF₃ CF₃ H F A-2131 H CF₃ OCH₃ H F A-2132 H CF₃ F F F A-2133 H CF₃ Cl F F A-2134 H CF₃ CH₃ F F A-2135 H CF₃ CF₃ F F A-2136 H CF₃ OCH₃ F F A-2137 H CF₃ F Cl F A-2138 H CF₃ Cl Cl F A-2139 H CF₃ CH₃ Cl F A-2140 H CF₃ CF₃ Cl F A-2141 H CF₃ OCH₃ Cl F A-2142 H CF₃ F CH₃ F A-2143 H CF₃ Cl CH₃ F A-2144 H CF₃ CH₃ CH₃ F A-2145 H CF₃ CF₃ CH₃ F A-2146 H CF₃ OCH₃ CH₃ F A-2147 H CF₃ F CF₃ F A-2148 H CF₃ Cl CF₃ F A-2149 H CF₃ CH₃ CF₃ F A-2150 H CF₃ CF₃ CF₃ F A-2151 H CF₃ OCH₃ CF₃ F A-2152 H CF₃ —O(CH₂)₂O— F A-2153 H CF₃ —OCH₂CH₂—^(#) F A-2154 H CF₃ —CH═CH—CH═CH— F A-2155 H CF₃ F H Cl A-2156 H CF₃ Cl H Cl A-2157 H CF₃ CH₃ H Cl A-2158 H CF₃ CF₃ H Cl A-2159 H CF₃ OCH₃ H Cl A-2160 H CF₃ F F Cl A-2161 H CF₃ Cl F Cl A-2162 H CF₃ CH₃ F Cl A-2163 H CF₃ CF₃ F Cl A-2164 H CF₃ OCH₃ F Cl A-2165 H CF₃ F Cl Cl A-2166 H CF₃ Cl Cl Cl A-2167 H CF₃ CH₃ Cl Cl A-2168 H CF₃ CF₃ Cl Cl A-2169 H CF₃ OCH₃ Cl Cl A-2170 H CF₃ F CH₃ Cl A-2171 H CF₃ Cl CH₃ Cl A-2172 H CF₃ CH₃ CH₃ Cl A-2173 H CF₃ CF₃ CH₃ Cl A-2174 H CF₃ OCH₃ CH₃ Cl A-2175 H CF₃ F CF₃ Cl A-2176 H CF₃ Cl CF₃ Cl A-2177 H CF₃ CH₃ CF₃ Cl A-2178 H CF₃ CF₃ CF₃ Cl A-2179 H CF₃ OCH₃ CF₃ Cl A-2180 H CF₃ —O(CH₂)₂O— Cl A-2181 H CF₃ —OCH₂CH₂—^(#) Cl A-2182 H CF₃ —CH═CH—CH═CH— Cl A-2183 H CF₃ F H CH₃ A-2184 H CF₃ Cl H CH₃ A-2185 H CF₃ CH₃ H CH₃ A-2186 H CF₃ CF₃ H CH₃ A-2187 H CF₃ OCH₃ H CH₃ A-2188 H CF₃ F F CH₃ A-2189 H CF₃ Cl F CH₃ A-2190 H CF₃ CH₃ F CH₃ A-2191 H CF₃ CF₃ F CH₃ A-2192 H CF₃ OCH₃ F CH₃ A-2193 H CF₃ F Cl CH₃ A-2194 H CF₃ Cl Cl CH₃ A-2195 H CF₃ CH₃ Cl CH₃ A-2196 H CF₃ CF₃ Cl CH₃ A-2197 H CF₃ OCH₃ Cl CH₃ A-2198 H CF₃ F CH₃ CH₃ A-2199 H CF₃ Cl CH₃ CH₃ A-2200 H CF₃ CH₃ CH₃ CH₃ A-2201 H CF₃ CF₃ CH₃ CH₃ A-2202 H CF₃ OCH₃ CH₃ CH₃ A-2203 H CF₃ F CF₃ CH₃ A-2204 H CF₃ Cl CF₃ CH₃ A-2205 H CF₃ CH₃ CF₃ CH₃ A-2206 H CF₃ CF₃ CF₃ CH₃ A-2207 H CF₃ OCH₃ CF₃ CH₃ A-2208 H CF₃ —O(CH₂)₂O— CH₃ A-2209 H CF₃ —OCH₂CH₂—^(#) CH₃ A-2210 H CF₃ —CH═CH—CH═CH— CH₃ A-2211 H CF₃ F H CF₃ A-2212 H CF₃ Cl H CF₃ A-2213 H CF₃ CH₃ H CF₃ A-2214 H CF₃ CF₃ H CF₃ A-2215 H CF₃ OCH₃ H CF₃ A-2216 H CF₃ F F CF₃ A-2217 H CF₃ Cl F CF₃ A-2218 H CF₃ CH₃ F CF₃ A-2219 H CF₃ CF₃ F CF₃ A-2220 H CF₃ OCH₃ F CF₃ A-2221 H CF₃ F Cl CF₃ A-2222 H CF₃ Cl Cl CF₃ A-2223 H CF₃ CH₃ Cl CF₃ A-2224 H CF₃ CF₃ Cl CF₃ A-2225 H CF₃ OCH₃ Cl CF₃ A-2226 H CF₃ F CH₃ CF₃ A-2227 H CF₃ Cl CH₃ CF₃ A-2228 H CF₃ CH₃ CH₃ CF₃ A-2229 H CF₃ CF₃ CH₃ CF₃ A-2230 H CF₃ OCH₃ CH₃ CF₃ A-2231 H CF₃ F CF₃ CF₃ A-2232 H CF₃ Cl CF₃ CF₃ A-2233 H CF₃ CH₃ CF₃ CF₃ A-2234 H CF₃ CF₃ CF₃ CF₃ A-2235 H CF₃ OCH₃ CF₃ CF₃ A-2236 H CF₃ —O(CH₂)₂O— CF₃ A-2237 H CF₃ —OCH₂CH₂—^(#) CF₃ A-2238 H CF₃ —CH═CH—CH═CH— CF₃ A-2239 F CF₃ F H H A-2240 F CF₃ Cl H H A-2241 F CF₃ CH₃ H H A-2242 F CF₃ CF₃ H H A-2243 F CF₃ OCH₃ H H A-2244 F CF₃ F F H A-2245 F CF₃ Cl F H A-2246 F CF₃ CH₃ F H A-2247 F CF₃ CF₃ F H A-2248 F CF₃ OCH₃ F H A-2249 F CF₃ F Cl H A-2250 F CF₃ Cl Cl H A-2251 F CF₃ CH₃ Cl H A-2252 F CF₃ CF₃ Cl H A-2253 F CF₃ OCH₃ Cl H A-2254 F CF₃ F CH₃ H A-2255 F CF₃ Cl CH₃ H A-2256 F CF₃ CH₃ CH₃ H A-2257 F CF₃ CF₃ CH₃ H A-2258 F CF₃ OCH₃ CH₃ H A-2259 F CF₃ F CF₃ H A-2260 F CF₃ Cl CF₃ H A-2261 F CF₃ CH₃ CF₃ H A-2262 F CF₃ CF₃ CF₃ H A-2263 F CF₃ OCH₃ CF₃ H A-2264 F CF₃ —O(CH₂)₂O— H A-2265 F CF₃ —OCH₂CH₂—^(#) H A-2266 F CF₃ —CH═CH—CH═CH— H A-2267 F CF₃ F H F A-2268 F CF₃ Cl H F A-2269 F CF₃ CH₃ H F A-2270 F CF₃ CF₃ H F A-2271 F CF₃ OCH₃ H F A-2272 F CF₃ F F F A-2273 F CF₃ Cl F F A-2274 F CF₃ CH₃ F F A-2275 F CF₃ CF₃ F F A-2276 F CF₃ OCH₃ F F A-2277 F CF₃ F Cl F A-2278 F CF₃ Cl Cl F A-2279 F CF₃ CH₃ Cl F A-2280 F CF₃ CF₃ Cl F A-2281 F CF₃ OCH₃ Cl F A-2282 F CF₃ F CH₃ F A-2283 F CF₃ Cl CH₃ F A-2284 F CF₃ CH₃ CH₃ F A-2285 F CF₃ CF₃ CH₃ F A-2286 F CF₃ OCH₃ CH₃ F A-2287 F CF₃ F CF₃ F A-2288 F CF₃ Cl CF₃ F A-2289 F CF₃ CH₃ CF₃ F A-2290 F CF₃ CF₃ CF₃ F A-2291 F CF₃ OCH₃ CF₃ F A-2292 F CF₃ —O(CH₂)₂O— F A-2293 F CF₃ —OCH₂CH₂—^(#) F A-2294 F CF₃ —CH═CH—CH═CH— F A-2295 F CF₃ F H Cl A-2296 F CF₃ Cl H Cl A-2297 F CF₃ CH₃ H Cl A-2298 F CF₃ CF₃ H Cl A-2299 F CF₃ OCH₃ H Cl A-2300 F CF₃ F F Cl A-2301 F CF₃ Cl F Cl A-2302 F CF₃ CH₃ F Cl A-2303 F CF₃ CF₃ F Cl A-2304 F CF₃ OCH₃ F Cl A-2305 F CF₃ F Cl Cl A-2306 F CF₃ Cl Cl Cl A-2307 F CF₃ CH₃ Cl Cl A-2308 F CF₃ CF₃ Cl Cl A-2309 F CF₃ OCH₃ Cl Cl A-2310 F CF₃ F CH₃ Cl A-2311 F CF₃ Cl CH₃ Cl A-2312 F CF₃ CH₃ CH₃ Cl A-2313 F CF₃ CF₃ CH₃ Cl A-2314 F CF₃ OCH₃ CH₃ Cl A-2315 F CF₃ F CF₃ Cl A-2316 F CF₃ Cl CF₃ Cl A-2317 F CF₃ CH₃ CF₃ Cl A-2318 F CF₃ CF₃ CF₃ Cl A-2319 F CF₃ OCH₃ CF₃ Cl A-2320 F CF₃ —O(CH₂)₂O— Cl A-2321 F CF₃ —OCH₂CH₂—^(#) Cl A-2322 F CF₃ —CH═CH—CH═CH— Cl A-2323 F CF₃ F H CH₃ A-2324 F CF₃ Cl H CH₃ A-2325 F CF₃ CH₃ H CH₃ A-2326 F CF₃ CF₃ H CH₃ A-2327 F CF₃ OCH₃ H CH₃ A-2328 F CF₃ F F CH₃ A-2329 F CF₃ Cl F CH₃ A-2330 F CF₃ CH₃ F CH₃ A-2331 F CF₃ CF₃ F CH₃ A-2332 F CF₃ OCH₃ F CH₃ A-2333 F CF₃ F Cl CH₃ A-2334 F CF₃ Cl Cl CH₃ A-2335 F CF₃ CH₃ Cl CH₃ A-2336 F CF₃ CF₃ Cl CH₃ A-2337 F CF₃ OCH₃ Cl CH₃ A-2338 F CF₃ F CH₃ CH₃ A-2339 F CF₃ Cl CH₃ CH₃ A-2340 F CF₃ CH₃ CH₃ CH₃ A-2341 F CF₃ CF₃ CH₃ CH₃ A-2342 F CF₃ OCH₃ CH₃ CH₃ A-2343 F CF₃ F CF₃ CH₃ A-2344 F CF₃ Cl CF₃ CH₃ A-2345 F CF₃ CH₃ CF₃ CH₃ A-2346 F CF₃ CF₃ CF₃ CH₃ A-2347 F CF₃ OCH₃ CF₃ CH₃ A-2348 F CF₃ —O(CH₂)₂O— CH₃ A-2349 F CF₃ —OCH₂CH₂—^(#) CH₃ A-2350 F CF₃ —CH═CH—CH═CH— CH₃ A-2351 F CF₃ F H CF₃ A-2352 F CF₃ Cl H CF₃ A-2353 F CF₃ CH₃ H CF₃ A-2354 F CF₃ CF₃ H CF₃ A-2355 F CF₃ OCH₃ H CF₃ A-2356 F CF₃ F F CF₃ A-2357 F CF₃ Cl F CF₃ A-2358 F CF₃ CH₃ F CF₃ A-2359 F CF₃ CF₃ F CF₃ A-2360 F CF₃ OCH₃ F CF₃ A-2361 F CF₃ F Cl CF₃ A-2362 F CF₃ Cl Cl CF₃ A-2363 F CF₃ CH₃ Cl CF₃ A-2364 F CF₃ CF₃ Cl CF₃ A-2365 F CF₃ OCH₃ Cl CF₃ A-2366 F CF₃ F CH₃ CF₃ A-2367 F CF₃ Cl CH₃ CF₃ A-2368 F CF₃ CH₃ CH₃ CF₃ A-2369 F CF₃ CF₃ CH₃ CF₃ A-2370 F CF₃ OCH₃ CH₃ CF₃ A-2371 F CF₃ F CF₃ CF₃ A-2372 F CF₃ Cl CF₃ CF₃ A-2373 F CF₃ CH₃ CF₃ CF₃ A-2374 F CF₃ CF₃ CF₃ CF₃ A-2375 F CF₃ OCH₃ CF₃ CF₃ A-2376 F CF₃ —O(CH₂)₂O— CF₃ A-2377 F CF₃ —OCH₂CH₂—^(#) CF₃ A-2378 F CF₃ —CH═CH—CH═CH— CF₃ A-2379 Cl CF₃ F H H A-2380 Cl CF₃ Cl H H A-2381 Cl CF₃ CH₃ H H A-2382 Cl CF₃ CF₃ H H A-2383 Cl CF₃ OCH₃ H H A-2384 Cl CF₃ F F H A-2385 Cl CF₃ Cl F H A-2386 Cl CF₃ CH₃ F H A-2387 Cl CF₃ CF₃ F H A-2388 Cl CF₃ OCH₃ F H A-2389 Cl CF₃ F Cl H A-2390 Cl CF₃ Cl Cl H A-2391 Cl CF₃ CH₃ Cl H A-2392 Cl CF₃ CF₃ Cl H A-2393 Cl CF₃ OCH₃ Cl H A-2394 Cl CF₃ F CH₃ H A-2395 Cl CF₃ Cl CH₃ H A-2396 Cl CF₃ CH₃ CH₃ H A-2397 Cl CF₃ CF₃ CH₃ H A-2398 Cl CF₃ OCH₃ CH₃ H A-2399 Cl CF₃ F CF₃ H A-2400 Cl CF₃ Cl CF₃ H A-2401 Cl CF₃ CH₃ CF₃ H A-2402 Cl CF₃ CF₃ CF₃ H A-2403 Cl CF₃ OCH₃ CF₃ H A-2404 Cl CF₃ —O(CH₂)₂O— H A-2405 Cl CF₃ —OCH₂CH₂—^(#) H A-2406 Cl CF₃ —CH═CH—CH═CH— H A-2407 Cl CF₃ F H F A-2408 Cl CF₃ Cl H F A-2409 Cl CF₃ CH₃ H F A-2410 Cl CF₃ CF₃ H F A-2411 Cl CF₃ OCH₃ H F A-2412 Cl CF₃ F F F A-2413 Cl CF₃ Cl F F A-2414 Cl CF₃ CH₃ F F A-2415 Cl CF₃ CF₃ F F A-2416 Cl CF₃ OCH₃ F F A-2417 Cl CF₃ F Cl F A-2418 Cl CF₃ Cl Cl F A-2419 Cl CF₃ CH₃ Cl F A-2420 Cl CF₃ CF₃ Cl F A-2421 Cl CF₃ OCH₃ Cl F A-2422 Cl CF₃ F CH₃ F A-2423 Cl CF₃ Cl CH₃ F A-2424 Cl CF₃ CH₃ CH₃ F A-2425 Cl CF₃ CF₃ CH₃ F A-2426 Cl CF₃ OCH₃ CH₃ F A-2427 Cl CF₃ F CF₃ F A-2428 Cl CF₃ Cl CF₃ F A-2429 Cl CF₃ CH₃ CF₃ F A-2430 Cl CF₃ CF₃ CF₃ F A-2431 Cl CF₃ OCH₃ CF₃ F A-2432 Cl CF₃ —O(CH₂)₂O— F A-2433 Cl CF₃ —OCH₂CH₂—^(#) F A-2434 Cl CF₃ —CH═CH—CH═CH— F A-2435 Cl CF₃ F H Cl A-2436 Cl CF₃ Cl H Cl A-2437 Cl CF₃ CH₃ H Cl A-2438 Cl CF₃ CF₃ H Cl A-2439 Cl CF₃ OCH₃ H Cl A-2440 Cl CF₃ F F Cl A-2441 Cl CF₃ Cl F Cl A-2442 Cl CF₃ CH₃ F Cl A-2443 Cl CF₃ CF₃ F Cl A-2444 Cl CF₃ OCH₃ F Cl A-2445 Cl CF₃ F Cl Cl A-2446 Cl CF₃ Cl Cl Cl A-2447 Cl CF₃ CH₃ Cl Cl A-2448 Cl CF₃ CF₃ Cl Cl A-2449 Cl CF₃ OCH₃ Cl Cl A-2450 Cl CF₃ F CH₃ Cl A-2451 Cl CF₃ Cl CH₃ Cl A-2452 Cl CF₃ CH₃ CH₃ Cl A-2453 Cl CF₃ CF₃ CH₃ Cl A-2454 Cl CF₃ OCH₃ CH₃ Cl A-2455 Cl CF₃ F CF₃ Cl A-2456 Cl CF₃ Cl CF₃ Cl A-2457 Cl CF₃ CH₃ CF₃ Cl A-2458 Cl CF₃ CF₃ CF₃ Cl A-2459 Cl CF₃ OCH₃ CF₃ Cl A-2460 Cl CF₃ —O(CH₂)₂O— Cl A-2461 Cl CF₃ —OCH₂CH₂—^(#) Cl A-2462 Cl CF₃ —CH═CH—CH═CH— Cl A-2463 Cl CF₃ F H CH₃ A-2464 Cl CF₃ Cl H CH₃ A-2465 Cl CF₃ CH₃ H CH₃ A-2466 Cl CF₃ CF₃ H CH₃ A-2467 Cl CF₃ OCH₃ H CH₃ A-2468 Cl CF₃ F F CH₃ A-2469 Cl CF₃ Cl F CH₃ A-2470 Cl CF₃ CH₃ F CH₃ A-2471 Cl CF₃ CF₃ F CH₃ A-2472 Cl CF₃ OCH₃ F CH₃ A-2473 Cl CF₃ F Cl CH₃ A-2474 Cl CF₃ Cl Cl CH₃ A-2475 Cl CF₃ CH₃ Cl CH₃ A-2476 Cl CF₃ CF₃ Cl CH₃ A-2477 Cl CF₃ OCH₃ Cl CH₃ A-2478 Cl CF₃ F CH₃ CH₃ A-2479 Cl CF₃ Cl CH₃ CH₃ A-2480 Cl CF₃ CH₃ CH₃ CH₃ A-2481 Cl CF₃ CF₃ CH₃ CH₃ A-2482 Cl CF₃ OCH₃ CH₃ CH₃ A-2483 Cl CF₃ F CF₃ CH₃ A-2484 Cl CF₃ Cl CF₃ CH₃ A-2485 Cl CF₃ CH₃ CF₃ CH₃ A-2486 Cl CF₃ CF₃ CF₃ CH₃ A-2487 Cl CF₃ OCH₃ CF₃ CH₃ A-2488 Cl CF₃ —O(CH₂)₂O— CH₃ A-2489 Cl CF₃ —OCH₂CH₂—^(#) CH₃ A-2490 Cl CF₃ —CH═CH—CH═CH— CH₃ A-2491 Cl CF₃ F H CF₃ A-2492 Cl CF₃ Cl H CF₃ A-2493 Cl CF₃ CH₃ H CF₃ A-2494 Cl CF₃ CF₃ H CF₃ A-2495 Cl CF₃ OCH₃ H CF₃ A-2496 Cl CF₃ F F CF₃ A-2497 Cl CF₃ Cl F CF₃ A-2498 Cl CF₃ CH₃ F CF₃ A-2499 Cl CF₃ CF₃ F CF₃ A-2500 Cl CF₃ OCH₃ F CF₃ A-2501 Cl CF₃ F Cl CF₃ A-2502 Cl CF₃ Cl Cl CF₃ A-2503 Cl CF₃ CH₃ Cl CF₃ A-2504 Cl CF₃ CF₃ Cl CF₃ A-2505 Cl CF₃ OCH₃ Cl CF₃ A-2506 Cl CF₃ F CH₃ CF₃ A-2507 Cl CF₃ Cl CH₃ CF₃ A-2508 Cl CF₃ CH₃ CH₃ CF₃ A-2509 Cl CF₃ CF₃ CH₃ CF₃ A-2510 Cl CF₃ OCH₃ CH₃ CF₃ A-2511 Cl CF₃ F CF₃ CF₃ A-2512 Cl CF₃ Cl CF₃ CF₃ A-2513 Cl CF₃ CH₃ CF₃ CF₃ A-2514 Cl CF₃ CF₃ CF₃ CF₃ A-2515 Cl CF₃ OCH₃ CF₃ CF₃ A-2516 Cl CF₃ —O(CH₂)₂O— CF₃ A-2517 Cl CF₃ —OCH₂CH₂—^(#) CF₃ A-2518 Cl CF₃ —CH═CH—CH═CH— CF₃ A-2519 CH₃ CF₃ F H H A-2520 CH₃ CF₃ Cl H H A-2521 CH₃ CF₃ CH₃ H H A-2522 CH₃ CF₃ CF₃ H H A-2523 CH₃ CF₃ OCH₃ H H A-2524 CH₃ CF₃ F F H A-2525 CH₃ CF₃ Cl F H A-2526 CH₃ CF₃ CH₃ F H A-2527 CH₃ CF₃ CF₃ F H A-2528 CH₃ CF₃ OCH₃ F H A-2529 CH₃ CF₃ F Cl H A-2530 CH₃ CF₃ Cl Cl H A-2531 CH₃ CF₃ CH₃ Cl H A-2532 CH₃ CF₃ CF₃ Cl H A-2533 CH₃ CF₃ OCH₃ Cl H A-2534 CH₃ CF₃ F CH₃ H A-2535 CH₃ CF₃ Cl CH₃ H A-2536 CH₃ CF₃ CH₃ CH₃ H A-2537 CH₃ CF₃ CF₃ CH₃ H A-2538 CH₃ CF₃ OCH₃ CH₃ H A-2539 CH₃ CF₃ F CF₃ H A-2540 CH₃ CF₃ Cl CF₃ H A-2541 CH₃ CF₃ CH₃ CF₃ H A-2542 CH₃ CF₃ CF₃ CF₃ H A-2543 CH₃ CF₃ OCH₃ CF₃ H A-2544 CH₃ CF₃ —O(CH₂)₂O— H A-2545 CH₃ CF₃ —OCH₂CH₂—^(#) H A-2546 CH₃ CF₃ —CH═CH—CH═CH— H A-2547 CH₃ CF₃ F H F A-2548 CH₃ CF₃ Cl H F A-2549 CH₃ CF₃ CH₃ H F A-2550 CH₃ CF₃ CF₃ H F A-2551 CH₃ CF₃ OCH₃ H F A-2552 CH₃ CF₃ F F F A-2553 CH₃ CF₃ Cl F F A-2554 CH₃ CF₃ CH₃ F F A-2555 CH₃ CF₃ CF₃ F F A-2556 CH₃ CF₃ OCH₃ F F A-2557 CH₃ CF₃ F Cl F A-2558 CH₃ CF₃ Cl Cl F A-2559 CH₃ CF₃ CH₃ Cl F A-2560 CH₃ CF₃ CF₃ Cl F A-2561 CH₃ CF₃ OCH₃ Cl F A-2562 CH₃ CF₃ F CH₃ F A-2563 CH₃ CF₃ Cl CH₃ F A-2564 CH₃ CF₃ CH₃ CH₃ F A-2565 CH₃ CF₃ CF₃ CH₃ F A-2566 CH₃ CF₃ OCH₃ CH₃ F A-2567 CH₃ CF₃ F CF₃ F A-2568 CH₃ CF₃ Cl CF₃ F A-2569 CH₃ CF₃ CH₃ CF₃ F A-2570 CH₃ CF₃ CF₃ CF₃ F A-2571 CH₃ CF₃ OCH₃ CF₃ F A-2572 CH₃ CF₃ —O(CH₂)₂O— F A-2573 CH₃ CF₃ —OCH₂CH₂—^(#) F A-2574 CH₃ CF₃ —CH═CH—CH═CH— F A-2575 CH₃ CF₃ F H Cl A-2576 CH₃ CF₃ Cl H Cl A-2577 CH₃ CF₃ CH₃ H Cl A-2578 CH₃ CF₃ CF₃ H Cl A-2579 CH₃ CF₃ OCH₃ H Cl A-2580 CH₃ CF₃ F F Cl A-2581 CH₃ CF₃ Cl F Cl A-2582 CH₃ CF₃ CH₃ F Cl A-2583 CH₃ CF₃ CF₃ F Cl A-2584 CH₃ CF₃ OCH₃ F Cl A-2585 CH₃ CF₃ F Cl Cl A-2586 CH₃ CF₃ Cl Cl Cl A-2587 CH₃ CF₃ CH₃ Cl Cl A-2588 CH₃ CF₃ CF₃ Cl Cl A-2589 CH₃ CF₃ OCH₃ Cl Cl A-2590 CH₃ CF₃ F CH₃ Cl A-2591 CH₃ CF₃ Cl CH₃ Cl A-2592 CH₃ CF₃ CH₃ CH₃ Cl A-2593 CH₃ CF₃ CF₃ CH₃ Cl A-2594 CH₃ CF₃ OCH₃ CH₃ Cl A-2595 CH₃ CF₃ F CF₃ Cl A-2596 CH₃ CF₃ Cl CF₃ Cl A-2597 CH₃ CF₃ CH₃ CF₃ Cl A-2598 CH₃ CF₃ CF₃ CF₃ Cl A-2599 CH₃ CF₃ OCH₃ CF₃ Cl A-2600 CH₃ CF₃ —O(CH₂)₂O— Cl A-2601 CH₃ CF₃ —OCH₂CH₂—^(#) Cl A-2602 CH₃ CF₃ —CH═CH—CH═CH— Cl A-2603 CH₃ CF₃ F H CH₃ A-2604 CH₃ CF₃ Cl H CH₃ A-2605 CH₃ CF₃ CH₃ H CH₃ A-2606 CH₃ CF₃ CF₃ H CH₃ A-2607 CH₃ CF₃ OCH₃ H CH₃ A-2608 CH₃ CF₃ F F CH₃ A-2609 CH₃ CF₃ Cl F CH₃ A-2610 CH₃ CF₃ CH₃ F CH₃ A-2611 CH₃ CF₃ CF₃ F CH₃ A-2612 CH₃ CF₃ OCH₃ F CH₃ A-2613 CH₃ CF₃ F Cl CH₃ A-2614 CH₃ CF₃ Cl Cl CH₃ A-2615 CH₃ CF₃ CH₃ Cl CH₃ A-2616 CH₃ CF₃ CF₃ Cl CH₃ A-2617 CH₃ CF₃ OCH₃ Cl CH₃ A-2618 CH₃ CF₃ F CH₃ CH₃ A-2619 CH₃ CF₃ Cl CH₃ CH₃ A-2620 CH₃ CF₃ CH₃ CH₃ CH₃ A-2621 CH₃ CF₃ CF₃ CH₃ CH₃ A-2622 CH₃ CF₃ OCH₃ CH₃ CH₃ A-2623 CH₃ CF₃ F CF₃ CH₃ A-2624 CH₃ CF₃ Cl CF₃ CH₃ A-2625 CH₃ CF₃ CH₃ CF₃ CH₃ A-2626 CH₃ CF₃ CF₃ CF₃ CH₃ A-2627 CH₃ CF₃ OCH₃ CF₃ CH₃ A-2628 CH₃ CF₃ —O(CH₂)₂O— CH₃ A-2629 CH₃ CF₃ —OCH₂CH₂—^(#) CH₃ A-2630 CH₃ CF₃ —CH═CH—CH═CH— CH₃ A-2631 CH₃ CF₃ F H CF₃ A-2632 CH₃ CF₃ Cl H CF₃ A-2633 CH₃ CF₃ CH₃ H CF₃ A-2634 CH₃ CF₃ CF₃ H CF₃ A-2635 CH₃ CF₃ OCH₃ H CF₃ A-2636 CH₃ CF₃ F F CF₃ A-2637 CH₃ CF₃ Cl F CF₃ A-2638 CH₃ CF₃ CH₃ F CF₃ A-2639 CH₃ CF₃ CF₃ F CF₃ A-2640 CH₃ CF₃ OCH₃ F CF₃ A-2641 CH₃ CF₃ F Cl CF₃ A-2642 CH₃ CF₃ Cl Cl CF₃ A-2643 CH₃ CF₃ CH₃ Cl CF₃ A-2644 CH₃ CF₃ CF₃ Cl CF₃ A-2645 CH₃ CF₃ OCH₃ Cl CF₃ A-2646 CH₃ CF₃ F CH₃ CF₃ A-2647 CH₃ CF₃ Cl CH₃ CF₃ A-2648 CH₃ CF₃ CH₃ CH₃ CF₃ A-2649 CH₃ CF₃ CF₃ CH₃ CF₃ A-2650 CH₃ CF₃ OCH₃ CH₃ CF₃ A-2651 CH₃ CF₃ F CF₃ CF₃ A-2652 CH₃ CF₃ Cl CF₃ CF₃ A-2653 CH₃ CF₃ CH₃ CF₃ CF₃ A-2654 CH₃ CF₃ CF₃ CF₃ CF₃ A-2655 CH₃ CF₃ OCH₃ CF₃ CF₃ A-2656 CH₃ CF₃ —O(CH₂)₂O— CF₃ A-2657 CH₃ CF₃ —OCH₂CH₂—^(#) CF₃ A-2658 CH₃ CF₃ —CH═CH—CH═CH— CF₃ A-2659 CF₃ CF₃ F H H A-2660 CF₃ CF₃ Cl H H A-2661 CF₃ CF₃ CH₃ H H A-2662 CF₃ CF₃ CF₃ H H A-2663 CF₃ CF₃ OCH₃ H H A-2664 CF₃ CF₃ F F H A-2665 CF₃ CF₃ Cl F H A-2666 CF₃ CF₃ CH₃ F H A-2667 CF₃ CF₃ CF₃ F H A-2668 CF₃ CF₃ OCH₃ F H A-2669 CF₃ CF₃ F Cl H A-2670 CF₃ CF₃ Cl Cl H A-2671 CF₃ CF₃ CH₃ Cl H A-2672 CF₃ CF₃ CF₃ Cl H A-2673 CF₃ CF₃ OCH₃ Cl H A-2674 CF₃ CF₃ F CH₃ H A-2675 CF₃ CF₃ Cl CH₃ H A-2676 CF₃ CF₃ CH₃ CH₃ H A-2677 CF₃ CF₃ CF₃ CH₃ H A-2678 CF₃ CF₃ OCH₃ CH₃ H A-2679 CF₃ CF₃ F CF₃ H A-2680 CF₃ CF₃ Cl CF₃ H A-2681 CF₃ CF₃ CH₃ CF₃ H A-2682 CF₃ CF₃ CF₃ CF₃ H A-2683 CF₃ CF₃ OCH₃ CF₃ H A-2684 CF₃ CF₃ —O(CH₂)₂O— H A-2685 CF₃ CF₃ —OCH₂CH₂—^(#) H A-2686 CF₃ CF₃ —CH═CH—CH═CH— H₃ A-2687 CF₃ CF₃ F H F A-2688 CF₃ CF₃ Cl H F A-2689 CF₃ CF₃ CH₃ H F A-2690 CF₃ CF₃ CF₃ H F A-2691 CF₃ CF₃ OCH₃ H F A-2692 CF₃ CF₃ F F F A-2693 CF₃ CF₃ Cl F F A-2694 CF₃ CF₃ CH₃ F F A-2695 CF₃ CF₃ CF₃ F F A-2696 CF₃ CF₃ OCH₃ F F A-2697 CF₃ CF₃ F Cl F A-2698 CF₃ CF₃ Cl Cl F A-2699 CF₃ CF₃ CH₃ Cl F A-2700 CF₃ CF₃ CF₃ Cl F A-2701 CF₃ CF₃ OCH₃ Cl F A-2702 CF₃ CF₃ F CH₃ F A-2703 CF₃ CF₃ Cl CH₃ F A-2704 CF₃ CF₃ CH₃ CH₃ F A-2705 CF₃ CF₃ CF₃ CH₃ F A-2706 CF₃ CF₃ OCH₃ CH₃ F A-2707 CF₃ CF₃ F CF₃ F A-2708 CF₃ CF₃ Cl CF₃ F A-2709 CF₃ CF₃ CH₃ CF₃ F A-2710 CF₃ CF₃ CF₃ CF₃ F A-2711 CF₃ CF₃ OCH₃ CF₃ F A-2712 CF₃ CF₃ —O(CH₂)₂O— F A-2713 CF₃ CF₃ —OCH₂CH₂—^(#) F A-2714 CF₃ CF₃ —CH═CH—CH═CH— F A-2715 CF₃ CF₃ F H Cl A-2716 CF₃ CF₃ Cl H Cl A-2717 CF₃ CF₃ CH₃ H Cl A-2718 CF₃ CF₃ CF₃ H Cl A-2719 CF₃ CF₃ OCH₃ H Cl A-2720 CF₃ CF₃ F F Cl A-2721 CF₃ CF₃ Cl F Cl A-2722 CF₃ CF₃ CH₃ F Cl A-2723 CF₃ CF₃ CF₃ F Cl A-2724 CF₃ CF₃ OCH₃ F Cl A-2725 CF₃ CF₃ F Cl Cl A-2726 CF₃ CF₃ Cl Cl Cl A-2727 CF₃ CF₃ CH₃ Cl Cl A-2728 CF₃ CF₃ CF₃ Cl Cl A-2729 CF₃ CF₃ OCH₃ Cl Cl A-2730 CF₃ CF₃ F CH₃ Cl A-2731 CF₃ CF₃ Cl CH₃ Cl A-2732 CF₃ CF₃ CH₃ CH₃ Cl A-2733 CF₃ CF₃ CF₃ CH₃ Cl A-2734 CF₃ CF₃ OCH₃ CH₃ Cl A-2735 CF₃ CF₃ F CF₃ Cl A-2736 CF₃ CF₃ Cl CF₃ Cl A-2737 CF₃ CF₃ CH₃ CF₃ Cl A-2738 CF₃ CF₃ CF₃ CF₃ Cl A-2739 CF₃ CF₃ OCH₃ CF₃ Cl A-2740 CF₃ CF₃ —O(CH₂)₂O— Cl A-2741 CF₃ CF₃ —OCH₂CH₂—^(#) Cl A-2742 CF₃ CF₃ —CH═CH—CH═CH— Cl A-2743 CF₃ CF₃ F H CH₃ A-2744 CF₃ CF₃ Cl H CH₃ A-2745 CF₃ CF₃ CH₃ H CH₃ A-2746 CF₃ CF₃ CF₃ H CH₃ A-2747 CF₃ CF₃ OCH₃ H CH₃ A-2748 CF₃ CF₃ F F CH₃ A-2749 CF₃ CF₃ Cl F CH₃ A-2750 CF₃ CF₃ CH₃ F CH₃ A-2751 CF₃ CF₃ CF₃ F CH₃ A-2752 CF₃ CF₃ OCH₃ F CH₃ A-2753 CF₃ CF₃ F Cl CH₃ A-2754 CF₃ CF₃ Cl Cl CH₃ A-2755 CF₃ CF₃ CH₃ Cl CH₃ A-2756 CF₃ CF₃ CF₃ Cl CH₃ A-2757 CF₃ CF₃ OCH₃ Cl CH₃ A-2758 CF₃ CF₃ F CH₃ CH₃ A-2759 CF₃ CF₃ Cl CH₃ CH₃ A-2760 CF₃ CF₃ CH₃ CH₃ CH₃ A-2761 CF₃ CF₃ CF₃ CH₃ CH₃ A-2762 CF₃ CF₃ OCH₃ CH₃ CH₃ A-2763 CF₃ CF₃ F CF₃ CH₃ A-2764 CF₃ CF₃ Cl CF₃ CH₃ A-2765 CF₃ CF₃ CH₃ CF₃ CH₃ A-2766 CF₃ CF₃ CF₃ CF₃ CH₃ A-2767 CF₃ CF₃ OCH₃ CF₃ CH₃ A-2768 CF₃ CF₃ —O(CH₂)₂O— CH₃ A-2769 CF₃ CF₃ —OCH₂CH₂—^(#) CH₃ A-2770 CF₃ CF₃ —CH═CH—CH═CH— CH₃ A-2771 CF₃ CF₃ F H CF₃ A-2772 CF₃ CF₃ Cl H CF₃ A-2773 CF₃ CF₃ CH₃ H CF₃ A-2774 CF₃ CF₃ CF₃ H CF₃ A-2775 CF₃ CF₃ OCH₃ H CF₃ A-2776 CF₃ CF₃ F F CF₃ A-2777 CF₃ CF₃ Cl F CF₃ A-2778 CF₃ CF₃ CH₃ F CF₃ A-2779 CF₃ CF₃ CF₃ F CF₃ A-2780 CF₃ CF₃ OCH₃ F CF₃ A-2781 CF₃ CF₃ F Cl CF₃ A-2782 CF₃ CF₃ Cl Cl CF₃ A-2783 CF₃ CF₃ CH₃ Cl CF₃ A-2784 CF₃ CF₃ CF₃ Cl CF₃ A-2785 CF₃ CF₃ OCH₃ Cl CF₃ A-2786 CF₃ CF₃ F CH₃ CF₃ A-2787 CF₃ CF₃ Cl CH₃ CF₃ A-2788 CF₃ CF₃ CH₃ CH₃ CF₃ A-2789 CF₃ CF₃ CF₃ CH₃ CF₃ A-2790 CF₃ CF₃ OCH₃ CH₃ CF₃ A-2791 CF₃ CF₃ F CF₃ CF₃ A-2792 CF₃ CF₃ Cl CF₃ CF₃ A-2793 CF₃ CF₃ CH₃ CF₃ CF₃ A-2794 CF₃ CF₃ CF₃ CF₃ CF₃ A-2795 CF₃ CF₃ OCH₃ CF₃ CF₃ A-2796 CF₃ CF₃ —O(CH₂)₂O— CF₃ A-2797 CF₃ CF₃ —OCH₂CH₂—^(#) CF₃ A-2798 CF₃ CF₃ —CH═CH—CH═CH— CF₃ ^(#)The oxygen atom is attached to the 2-position

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-B, wherein A is a radical A.1 with R^(5a) being methyl and R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-B.1 to I.1′-B.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-C, wherein A is a radical A.1 with R^(5a) and R^(5b) being methyl, and R^(5c), R^(5d), R^(5f) and R^(5e) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-C.1 to I′.1-C.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-D, wherein A is a radical A.1 with R^(5c) and R^(5d) being methyl, and R^(5a), R^(5b), R^(5f) and R^(5e) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-D.1 to I′.1-D.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-E, wherein A is a radical A.1 with R^(5c) being phenyl and R^(5a), R^(5b), R^(5d), R^(5e) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-E.1 to I.1′-E.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-F, wherein A is a radical A.1 with R^(5a) being phenyl and R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-F.1 to I.1′-F.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-G, wherein A is a radical A.1 with R^(5a) being 4-bromophenyl and R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-G.1 to I.1′-G.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-H, wherein A is a radical A.1 with R^(5a), R^(5b), R^(5e) and R^(5f) being hydrogen and R^(5c) and R^(5d) form together a bivalent radical —CH₂(CH₂)₂CH₂—,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-H.1 to I.1′-H.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-I, wherein A is a radical A.1 with R^(5a), R^(5b), R^(5e) and R^(5f) being hydrogen and R^(5c) and R^(5d) form together a bivalent radical —CH₂(CH₂)₃CH₂—,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-I.1 to I.1-I.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I.1-K, wherein A is a radical A.1 with R^(5e) being phenyl and R^(5a), R^(5b), R^(5c), R^(5d) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I.1-K.1 to I.1′-K.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.1-L, wherein A is a radical A.1 with R^(5e) being 4-bromophenyl and R^(5a), R^(5b), R^(5c), R^(5d) and R^(5f) being hydrogen,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.1-L.1 to I.1′-L.2798).

Amongst compounds of the formula I′, preference is given to the following compounds of the formula I′.2-A, wherein A is a radical A.2 with R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen and R⁶ being methyl,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given above. Examples of these compounds are those wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.2-A.1 to I′.2-A.2798).

Amongst compounds of the formula I′, preference is given to the following compounds of the formula I′.2-B, wherein A is a radical A.2 with R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen and R⁶ being ethyl,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given above. Examples of these compounds are those wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.2-B.1 to I′.2-B.2798).

Amongst compounds of the formula I′, preference is given to the following compounds of the formula I′.2-C, wherein A is a radical A.2 with R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen and R⁶ being acetyl,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given above. Examples of these compounds are those wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.2-C.1 to I′.2-C.2798).

Amongst compounds of the formula I′, preference is also given to the following compounds of the formula I′.2-D, wherein A is a radical A.2 with R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) being hydrogen and R⁶ being methoxycarbonyl,

wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given above. Examples of these compounds are those wherein the radicals R^(1a), R^(1b), R^(2a), R^(2b) and R^(2c) have the meanings given in each line of table A (Compounds I′.2-D.1 to I′.2-D.2798).

The compounds of the formula I can be obtained for example by the methods outlined in scheme 1 or described below.

Compounds of formula I, wherein A is a radical A.1, can be obtained as outlined in scheme 1.

In scheme 1, the indices n and m, the radicals R¹, R², R³, R⁴, R^(5a), R^(5b), R^(5c), R^(5d), R^(5e), R^(5f) and R⁷ have one of the meanings given above. LG denotes a leaving group such as halogen, e.g. chlorine or bromine, OR′ or SR′ with R′ being C₁-C₆-alkyl, preferably chlorine, methoxy, ethoxy, methylthio or ethylthio.

According to the method outlined in scheme 1, compounds of formula I.1 may be obtained by reacting a 1,2-diphenylaminoethane of formula II with a 3,4-dihydro-2H-pyrrole of formula III, for example as outlined in preparation example 1. The reaction is usually carried out in a polar protic solvent. Examples of suitable protic solvents are C₁-C₆-alkanols, such as methanol, ethanol, n-propanol, isopropanol or carbonic acids having for example 1 to 10 carbon atoms, e. g. acetic acid. In cases where alkanols are used as solvents the addition of an acid (e.g. acetic acid) to the reaction may shorten reaction times and increase yields. The reaction is usually carried out at temperatures between room temperature and the boiling temperature of the solvent. It may be advantageous to carry out the reaction under microwave irradiation. Preferred is the use of microwave heating to increase reaction rates.

Compounds of formula I, wherein A in formula I is a radical A.2 (i.e. compounds of formula (I.2)) with R⁶ being different from hydrogen or a radical A.1 (i.e. compounds of formula (I.1)) with R⁷ being different from hydrogen, can be obtained from compounds of the formula I with R⁶ (or R⁷, respectively) being hydrogen as a starting material.

For example, compounds, for which R⁶ or R⁷ is C₁-C₆-alkyl or C₁-C₆-alkylcarbonyl can be prepared from compounds of formula I by reaction with suitable alkylating or acylating reagents R^(i)-L, wherein L is a leaving group such as halogen and R^(i) is C₁-C₆-alkyl or C₁-C₆-alkylcarbonyl. The transformation can be carried out by routine methods described in standard textbooks on organic synthesis (see, for example, J. March, Advanced Organic Synthesis, 4^(th) ed. John Wiley and Sons.)

To obtain compounds of formula I, wherein R⁶ or R⁷ denotes C₁-C₆-alkyloxycarbonyl or C₁-C₆-alkylthiocarbonyl, the starting material of formula I.1 with R⁷ being hydrogen is reacted with a suitable haloformiate of the formula R^(k)—C(O)-Hal, wherein Hal is halogen, especially chlorine, and R^(k) is C₁-C₆-alkyloxy or C₁-C₆-alkylthio. The transformation can be carried out by routine methods well known to those skilled in the art (see, for example, J. March, Advanced Organic Synthesis, 4^(th) ed. John Wiley and Sons.).

To obtain compounds of formula I, wherein R⁶ or R⁷ denotes the cyano group, the cyano group can be introduced by cyanation of compounds of formula I.1 with R⁷ being hydrogen using e.g. cyanogen bromide (CNBr). The reaction is carried out according to standard methods well known to those skilled in the art.

To obtain compounds of formula I, wherein R⁶ or R⁷ denotes the nitro group, the nitro group can be introduced by nitration of compounds of formula I.1 with R⁷ being hydrogen using a nitronium source according to standard methods well known to those skilled in the art.

The group S(═O)₂NR^(c)R^(d) can be introduced as a radical R⁶ or R⁷ for example by reacting a compound of formula I.1 with R⁷ being hydrogen with a chlorosulfonamide reagent Cl—S(═O)₂NR^(c)R^(d) according to routine methods described in standard textbooks on organic synthesis, see e.g. J. March, Advanced Organic Synthesis, 3^(rd) ed. John Wiley and Sons. Furthermore, the group C(═O)NR^(c)R^(d) can be introduced as a radical R⁶ or R⁷ by reacting a compound of formula I.1 with R⁷ being hydrogen with chloroformamides Cl—C(═O)NR^(c)R^(d) or with isocyanates OCN—R^(c) for R^(d) being hydrogen.

1,2-Diphenylethylamines of formula II are known in the art (e.g. 1,2-diphenylethylamine, CAS-Nr. [3082-58-4]) or can be prepared by methods well known to those skilled in the art. Suitable methods for preparing 1,2-diphenylethylamines of formula II include inter alia the reductive amination of the corresponding phenylbenzylketones or the reduction of the corresponding phenylbenzyloximes (see, for example, J. Med. Chem. 1995, 38, 1600-1607 or J. Med. Chem. 1994, 37 (7), 913-923). Furthermore, compounds of formula II can be prepared by addition of phenyl- or benzyl-organometallic reagents to suitable imines (e.g. t-butylsulfinylimine) derived from (substituted) benzaldehyde- or phenyl-acetaldehyde precursors according to the method described in Tetrahedron 1999, 55, 8883-8904.

3,4-Dihydro-2H-pyrroles of formula III, for which LG denotes a leaving group such as Cl or OR′ (see, for example, J. Med. Chem. 2001, 44, 1588-1593), or SR′ (see, for example ibid. or Tetrahedron Lett. 2003, 44 (7), 1437-1440) are known and can be prepared according to routine methods, which are familiar to an organic chemist. 3,4-Dihydro-2H-pyrrole compounds of formula III, for which LG denotes Cl, can be obtained from the corresponding lactams by treatment with dehydrating reagents such as POCl₃ or PCl₅ in an aprotic solvent such as methylene chloride or benzene (see, for example, Asian J. Chem. 2005, 17 (3), 1641-1645 or J. Heterocycl. Chem. 1989, 26 (3), 821-828).

These lactam starting materials can also be alkylated to give the lactim building blocks of formula (III) for which LG equals OR′. Preferred alkylating reagents are trialkyloxonium tetrafluoroborate, dimethylsulfate or methyl iodide. Alkylation of the corresponding thiolactams, which can for example be derived from the respective lactams by treatment with Lawesson's reagent, furnishes 3,4-dihydro-2H-pyrroles (III) for which LG equals SR′ (For both cases, see, for example, J. Med. Chem. 2001, 44, 1588-1593).

As a rule, the compounds of the formula I can be prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds I can advantageously be prepared from other compounds I by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.

Due to their excellent activity, the compounds of formula may be used for controlling animal pests.

Accordingly, the present invention also provides a method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof or a composition as defined above.

Preferably, the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from animal pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the formula I or an agriculturally acceptable salt thereof as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the “substrate” (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.

In the sense of the present invention, “animal pests” are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes.

The invention further provides an agricultural composition for combating such animal pests, which comprises such an amount of at least one compound of formula I or at least one agriculturally useful salt thereof and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.

Such a composition may contain a single active compound of formula I or a salt thereof or a mixture of several active compounds of formula I or their salts according to the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers as well as individual tautomers or mixtures of tautomers.

The compounds of the formula I and the pestidicidal compositions comprising them are effective agents for controlling arthropod pests and nematodes. Animal pests controlled by the compounds of formula I include for example:

insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus soistitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12 punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;

dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;

thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;

hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;

heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;

homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphldula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Brachycaudus cardui, Brachycaudus helichrysi, Brachy-caudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordman-nianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactu-cae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus as-calonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosi-phum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;

termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus and Termes natalensis;

orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;

Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis;

Siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp;

The compositions and compounds of formula I are useful for the control of nematodes, especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species;

cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Paratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

In a preferred embodiment of the invention the compounds of formula I are used for controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina, in particular acaridae. The compounds of the formula I according to the present invention are particularly useful for controlling insects of the order Thysanoptera and Homoptera.

The compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, in particular invertebrate pest, especially insects or arachnids such as acaridae by contacting the plant/crop with a pesticidally effective amount of compounds of formula I. The term “crop” refers both to growing and harvested crops.

The compounds of formula I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; In each case, It should ensure a fine and even distribution of the compound according to the invention.

The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-foaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.

Suitable carriers include liquid and solid carriers. Examples of suitable solvents or liquid carriers are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone [NMP], N-octylpyrrolidone [NOP]), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.

Suitable emulsifiers are non-ionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

A suitable preservative is e.g. dichlorophen.

Seed treatment formulations may additionally comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

An example for a gelling agent is carrageen (Satiagel®).

Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules can be prepared by binding the active compounds to solid carriers.

Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). In this case, the active compound(s) are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.

The compounds of formula I can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% per weight.

The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.

The Following are Examples of Formulations:

1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

A) Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a formulation with 10% (w/w) of active compound(s) is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.

C) Emulsifiable Concentrates (EC)

15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

I) Dustable Powders (DP, DS)

5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s)

J) Granules (GR, FG, GG, MG)

0.5 parts by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.

K) ULV Solutions (UL)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.

The compounds of formula I are also suitable for the treatment of plant propagation materials (such as seed). Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having preger-minated the latter

In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Other preferred FS formulations of compounds of formula I for seed treatment comprise from 0.5 to 80 wt % of the active ingredient, from 0.05 to 5 wt % of a wetter, from 0.5 to 15 wt % of a dispersing agent, from 0.1 to 5 wt % of a thickener, from 5 to 20 wt % of an anti-freeze agent, from 0.1 to 2 wt % of an anti-foam agent, from 1 to 20 wt % of a pigment and/or a dye, from 0 to 15 wt % of a sticker/adhesion agent, from 0 to 75 wt % of a filler/vehicle, and from 0.01 to 1 wt % of a preservative.

Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

The compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).

For use against ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches, compounds of formula I are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickiness, moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitoes or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250° C., dimethylfomamide, N-methylpyrrolidone, dimethyl sulphoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used.

The compounds of formula I and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are N,N-diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the active compounds of formula I or spraying them onto the nets.

Methods which can be employed for treating the plant propagation material, in particular the seed, are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, “seed treatment” refers to all methods that bring plant propagation material, in particular seeds, and the compounds of formula I into contact with each other, and “seed dressing” to methods of seed treatment which provide the seeds with an amount of the compounds of formula I, i.e. which generate a plant propagation material, in particular the seed comprising the compound of formula I. In principle, the treatment can be applied to the plant propagation material, in particular to the seed at any time from the harvest of the plant propagation material, in particular of the seed to the sowing of the plant propagation material, in particular of the seed. The plant propagation material, in particular the seed, can be treated immediately before, or during, the planting of the plant propagation material, in particular of the seed, for example using the “planter's box” method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown plant propagation material, in particular to unsown seed. As used herein, the term “un-sown seed” is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the plant propagation material, in particular the seed, is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying step.

The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.

A further object of the present invention is therefore to provide new methods for controlling parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.

The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a non-therapeutic method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.

The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.

The term “animals” in or on which parasites should be controlled refers in particular to warm blooded animals including mammals and birds, as well as fish, reptiles and amphibians. The term “parasites” relates in particular to invertebrates which are likely to infest or attack warm blooded animals including mammals and birds.

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises including a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof into a composition comprising it for treating, controlling, preventing or protecting animals against infestation or infection by parasites.

The invention further relates to the use of compounds of formula I for treating, controlling, preventing or protecting animals against infestation or infection by parasites.

The invention relates also to the use of a compound of the formula I, or a composition comprising it, for the manufacture of a medicament for the therapeutic treatment of animals against infections or infestions by parasites.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, nonemetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly, it has been found that compounds of formula I are suitable for combating endo- and ectoparasites in and on animals.

Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.

Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

The compounds of formula I are especially useful for combating ectoparasites.

The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria—Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus,

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,

actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,

bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm),

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of compounds of formula I and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of formula I and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of formula I and compositions containing them for combating fleas is especially preferred.

The use of the compounds of formula I and of the compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The compounds of formula I also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

The compounds of formula I can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).

The present invention relates to the therapeutic and the non-therapeutic use of compounds of formula I for controlling and/or combating parasites in and/or on animals.

The compounds of formula I may be used to protect the animals from attack or infestation by parasites by contacting them with a parasitically effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the parasite, e.g. also at it's locus, and optionally also administrating the compounds/composition directly on the animal) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of compounds of formula I.

“Locus” as defined above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal. The compounds of the invention can also be applied preventively to places at which occurrence of the pests or parasites is expected.

Administration to the animal can be carried out both prophylactically and therapeutically.

Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, the compounds of formula I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of formulae I may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds of formula I, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of formula I may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of formula I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of formula I may be formulated into an implant for subcutaneous administration. In addition the compounds of formula I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds of formula I.

The compounds of formula I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds of formula I. In addition, the compounds of formula I may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable Preparations are:

Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents are water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-alkylpyrrolidones such as methylpyrrolidone, N-butylpyrrolidone or N-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable Hydrophobic Phases (Oils) are:

liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C₈-C₁₂ or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C₈-C₁₀ fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C₁₆-C₁₈, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C₁₂-C₁₈, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyl-dodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.

Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable Emulsifiers are:

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin;

anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;

cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compounds of formula I.

Generally, it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.

Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.

In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I are applied dermally/topically.

In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally, it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.

Compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

These agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds of formula I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.

The following list M of pesticides together with which the compounds according to the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

M.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate, heptenophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

M.2. Carbamates: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate;

M.3. Pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin(pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tralomethrin and transfluthrin;

M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene, fenoxycarb and pyriproxyfen;

M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium and AKD1022;

M.6. GABA gated chloride channel antagonist compounds: chlordane, endosulfan, gamma-HCH (lindane); ethiprole, fipronil, pyrafluprole and pyriprole;

M.7. Chloride channel activators: abamectin, emamectin benzoate, milbemectin, lepimectin;

M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;

M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;

M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;

M.11. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon;

M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

M.13. Synergists: piperonyl butoxide, tribufos;

M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;

M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;

M.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;

M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;

M.18. Chitin synthesis inhibitors: buprofezin, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;

M.20. Octapaminergic agonists: amitraz;

M.21. Ryanodine receptor modulators: flubendiamide and (R)- and (S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid (M21.1);

M.22. Various: aluminium phosphide, amidoflumet, benclothiaz, benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate, phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur compounds, tartar emetic, sulfoxaflor, 4-but-2-ynyloxy-6-(3,5-dimethyl-piperidin-1-yl)-2-fluoro-pyrimidine (M22.1), 3-benzoylamino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2-fluoro-benzamide (M22.2), 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide (M22.3), 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamide (M22.4), 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-thiazol-2-ylmethyl-benzamide (M22.5), 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzamide (M22.6), 4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (M22.7), 4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one (M22.8), 4-{[(2-chloro-1,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (M22.9), 4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (M22.10), 4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one (M22.11), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (M22.12), 4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (M22.13), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (M22.14), 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (M22.15), 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (M22.16), cyclopropaneacetic acid, 1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester (M22.17), 8-(2-cyclopropylmethoxy-4-methyl-phenoxy)-3-(6-methyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (M22.18);

M.23. N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone or N—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone, wherein R′ is methyl or ethyl, halo is chloro or bromo, R′ is hydrogen or methyl and R′″ is methyl or ethyl;

M.24. Anthranilamides: chloranthraniliprole, cyantraniliprole, 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[4-cyano-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M24.1), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-chloro-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M24.2), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-bromo-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M24.3), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2-bromo-4-chloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M24.4), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[2,4-dichloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M24.5), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid[4-chloro-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M24.6);

M.25. Malononitrile compounds: CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₃, (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-propyl)malononitrile), CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₂CF₃ (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile);

M.26. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis;

The commercially available compounds of the group M may be found in The Pesticide Manual, 13th Edition, British Crop Protection Council (2003) among other publications.

Thioamides of formula M6.1 and their preparation have been described in WO 98/28279. Lepimectin is known from Agro Project, PJB Publications Ltd, November 2004. Benclothiaz and its preparation have been described in EP-A1 454621. Methidathion and Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Acetoprole and its preparation have been described in WO 98/28277. Metaflumizone and its preparation have been described in EP-A1 462 456. Flupyrazofos has been described in Pesticide Science 54, 1988, p. 237-243 and in U.S. Pat. No. 4,822,779. Pyrafluprole and its preparation have been described in JP 2002193709 and in WO 01/00614. Pyriprole and its preparation have been described in WO 98/45274 and in U.S. Pat. No. 6,335,357. Amidoflumet and its preparation have been described in U.S. Pat. No. 6,221,890 and in JP 21010907. Flufenerim and its preparation have been described in WO 03/007717 and in WO 03/007718. AKD 1022 and its preparation have been described in U.S. Pat. No. 6,300,348. Chloranthraniliprole has been described in WO 01/70671, WO 03/015519 and WO 05/118552. Cyantraniliprole has been described in WO 01/70671, WO 04/067528 and WO 05/118552. The anthranilamides M 24.1 to M 24.6 have been described in WO 2008/72743 and WO 200872783. The phthalamide M 21.1 is known from WO 2007/101540. Cyflumetofen and its preparation have been described in WO 04/080180. The aminoquinazolinone compound pyrifluquinazon has been described in EP A 109 7932. Sulfoximine sulfoxaflor has been described in WO 2006/060029 and WO 2007/149134. The alkynylether compound M22.1 is described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The carboxamide compound M 22.2 is known from WO 2007/83394. The oxazoline compounds M 22.3 to M 22.6 have been described in WO 2007/074789. The furanon compounds M 22.7 to M 22.16 have been described e.g. in WO 2007/115644. The pyripyropene derivative M 22.17 has been described in WO 2008/66153 and WO 2008/108491. The pyridazin compound M 22.18 has been described in JP 2008/115155. The malononitrile compounds have been described in WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.

Fungicidal mixing partners are in particular those selected from the group consisting of acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,

amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamin, tridemorph,

anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,

antibiotics such as cycloheximid, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,

azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizol, triticonazole, flutriafol,

dicarboximides such as iprodion, myclozolin, procymidon, vinclozolin,

dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb,

heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazole, triforine,

copper fungicides such as Bordeaux mixture, copper acetate, copper oxychloride, basic copper sulfate,

nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthalisopropyl, phenylpyrroles such as fenpiclonil or fludioxonil,

sulfur,

other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamid,

strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin or trifloxystrobin,

sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid, cinnemamides and analogs such as dimethomorph, flumetover or flumorph.

The animal pest, i.e. arthropodes and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compound(s) of formula I or composition(s) containing them by any application method known in the art. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).

Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

“Locus” means a habitat, breeding ground, cultivated plants, plant propagation material (such as seed), soil, area, material or environment in which a pest or parasite is growing or may grow.

In general “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

The compounds of formula I and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywood, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

The compounds of formula I can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent and/or insecticide.

For use in bait compositions, the typical content of active ingredient is from 0.001% by weight to 15% by weight, desirably from 0.001% by weight to 5% by weight of active compound.

For use in spray compositions, the content of active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and most preferably from 0.01 to 15% by weight.

For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

In the treatment of seed, the application rates of the active ingredients are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed.

The present invention is now illustrated in further detail by the following examples.

A) PREPARATION EXAMPLES

The compounds of formula I were characterized by coupled High Performance Liquid Chromatography/mass spectroscopy (HPLC/MS), by NMR or by their melting points. HPLC: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA in a ratio of from 5:95 to 95:5 in 5 minutes at 40° C. MS: Quadrupol electrospray ionisation, 80 V (positive modus).

A.1) Preparation of Compounds of Formula I Example 7 [5-(4-Bromo-phenyl)-4,5-dihydro-3H-pyrrol-2-yl]-(1,2-diphenyl-ethyl)-amine (Compound Example 7 of Table I)

A solution of 1,2-diphenyl-ethylamine (500 mg, 2.5 mmol) and 2-(4-bromo-phenyl)-5-methoxy-3,4-dihydro-2H-pyrrole (770 mg, 3.04 mmol) in isopropanol (3 mL) was stirred at 150° C. for 1 h under microwave irradiation (300 W). The resulting suspension was concentrated under reduced pressure. Flash column chromatography purification (NH₂-modified SiO₂, gradient of cyclohexane/ethyl acetate) of the residue yielded 580 mg (55%) of the desired product as a colorless solid.

The compounds of formula I.1 shown in table I hereinafter (examples 1 to 19), wherein (R¹)_(n), (R²)_(m), R^(5a), R^(5b), R^(5c) and R^(5d) independently from one another have one of the meanings given in table I have been prepared in analogy to the preparation example 1 shown hereinbefore.

TABLE I (I.1)

Physico- chemical data (m.p. Ex. (R¹)_(n) (R²)_(m) R^(5a) R^(5b) R^(5c) R^(5d) [° C.], r.t., M⁺)  1 — — H H H H n.d., 2.37, 265.1  2 — — CH₃ CH₃ H H n.d., 2.55, 292.9  3 — — H H —CH₂(CH₂)₃CH₂— n.d., 3.01, 332.9  4 — — H H CH₃ CH₃ 106-107, 2.72, 293.1  5 — — CH₃ H H H n.d., 2.49, 279.1  6 — — H H C₆H₅ H n.d., 3.07, 341.2  7** — — H H H H 130-134, 3.04, 418.7  8 3-CH₃, 2-CH₃, H H H H 129-130, n.d. 5-CH₃ 3-CH₃  9 3-CH₃, 2-CH₃, CH₃ CH₃ H H n.d., 3.21, 348.5 5-CH₃ 3-CH₃ 10 3-CH₃, 2-CH₃, H H —CH₂(CH₂)₃CH₂— n.d., 3.58, 388.9 5-CH₃ 3-CH₃ 11 3-CH₃, 2-CH₃, H H CH₃ CH₃ 55-56, 3.17, 5-CH₃ 3-CH₃ 348.9 12 3-CH₃, 2-CH₃, CH₃ H H H n.d., 3.14, 335.2 5-CH₃ 3-CH₃ 13 3-CH₃, 2-CH₃, H H C₆H₅ H n.d., 3.38, 396.9 5-CH₃ 3-CH₃ 14 3-CH₃, 2-CH₃, 4-Br—C₆H₅ H H H n.d., 3.66, 475.1 5-CH₃ 3-CH₃ 15 3-CH₃, 2-Cl, H H H H n.d., 3.06, 360.8 5-CH₃ 3-Cl 16 3-CH₃ 2-CH₃, H H H H n.d., 2.97, 307.3 3-CH₃ 17 3-CH₃, 2,3- H H H H n.d., 2.83, 351.2 5-CH₃ O(CH₂)₂O— 18 3-CH₃, 2,3-annulated H H H H n.d., 3.20, 343.0 5-CH₃ phenyl 19 3-CH₃, 2,3- H H H H n.d., 2.98, 335.0 5-CH₃ OCH₂CH₂— 20 — — 4-Br—C₆H₄ H H H M⁺ = 418.7 21** 3-CH₃, 2-CH₃, H H H H M⁺ = 475.1 5-CH₃ 3-CH₃ Ex. = example m.p. = melting point r.t. = retention time M⁺ = molecular mass of the detected cationic species n.d. = not determined **Compound of the formula I with R³, R⁴ = H, R^(5f) = H and R^(5e) = 4-Br—C₆H₄

B) BIOLOGICAL EXAMPLES

Action Against Pests:

The action of the compounds of the general formulae I and II against pests was evaluated by the following experiments:

I. Cotton Aphid (Aphis gossypii)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Cotton plants in the cotyledon stage (variety Delta Pine) are infested with approximately 100 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hours. The cotyledons of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, the compounds of examples 8, 17, 18 and 19 at 300 ppm showed over 75% mortality in comparison with untreated controls.

II. Green Peach Aphid (Myzus persicae)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Pepper plants in the 2nd leaf-pair stage (variety ‘California Wonder’) are infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hours. The leaves of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, the compounds of examples 8, 9, 12, 15, 16, 17, 18 and 19, respectively, at 2500 ppm showed over 90% mortality in comparison with untreated controls.

III. Cowpea Aphid (Aphis craccivora)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Potted cowpea plants colonized with 100-150 aphids of various stages were sprayed after the pest population has been recorded. Population reduction was recorded after 24, 72, and 120 hours.

In this test, the compounds of examples 8, 15 and 16, respectively, at 300 ppm showed over 90% mortality in comparison with untreated controls.

IV. Silverleaf Whitefly (bemisia argentifolii, Adult)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Selected cotton plants were grown to the cotyledon state (one plant per pot). The cotyledons were dipped into the test solution to provide complete coverage of the foliage and placed in a well-vented area to dry. Each pot with treated seedling was placed in a plastic cup and 10 to 12 whitefly adults (approximately 3-5 day old) were introduced. The insects were colleted using an aspirator and a 0.6 cm, non-toxic Tygon® tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. The cups were covered with a re-usable screened lid (150 micron mesh polyester screen PeCap from Tetko Inc). Test plants were maintained in the holding room at about 25° C. and 20-40% relative humidity for 3 days avoiding direct exposure to the fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment of the plants.

In this test, the compounds of examples 8, 18 and 19, respectively, at 300 ppm showed over 70% mortality in comparison to untreated controls. 

1. A compound of formula (I)

wherein n is 0, 1, 2, 3, 4 or 5; m is 0, 1, 2, 3, 4 or 5; wherein at least one of the indices n and m is different from 0; R¹ and R² are independently selected from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, formyl, C₁-C₆-alkylcarbonyl, —C(═O)OH, C₁-C₆-alkoxycarbonyl, —C(═O)NH₂, C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl, —OH, C₁-C₆-alkoxy, —SH, C₁-C₆-alkylthio, —NH₂, C₁-C₆-alkylamino and di(C₁-C₆-alkyl)amino, wherein alkyl and the alkyl moiety of alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylthio, alkylamino and dialkylamino may be partially or completely halogenated and/or may carry any combination of 1, 2 or 3 substituents, independently of one another selected from the group consisting of CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C₁-C₆-alkylthio, wherein C₃-C₈-cycloalkyl is unsubstituted or may carry any combination of 1, 2 or 3 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl, CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C₁-C₆-alkylthio, and/or two radicals R¹ bound to adjacent carbon atoms of the phenyl ring and/or two radicals R² bound to adjacent carbon atoms of the phenyl ring together with said carbon atoms form a fused benzene, a fused saturated or partially unsaturated 5- or 6-membered carbocycle or a fused 5- or 6-membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, wherein each fused benzene, carbocycle or heterocycle is unsubstituted or carries 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, CN, NO₂, OH, SH, NH₂, COOH, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio; R³ and R⁴ are selected each independently of one another from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, and C₂-C₆-alkynyl, wherein the last 3 radicals mentioned may be partly or completely halogenated and/or may carry any combination of 1, 2 or 3 radicals selected independently of one another from the group consisting of CN, NO₂, —OR^(b), NR^(c)R^(d), —SR^(e), —C(═O)R^(a) and —C(═O)OR^(b), C₃-C₆-cycloalkyl, phenyl and benzyl, wherein C₃-C₆-cycloalkyl, phenyl and benzyl may carry 1, 2, 3, 4 or 5 substituents selected independently of one another from the group consisting of halogen, CN, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₆-haloalkyl, —OR^(b), NR^(c)R^(d), —SR^(e)—C(═O)R^(a) and —C(═O)OR^(b); A is a radical of the formulae A.1 or A.2,

wherein * indicates the point of attachment to the remaining part of the compound; R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) are selected independently from one another from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl and Ar², wherein C₁-C₆-alkyl and the alkyl moiety in C₁-C₆-alkoxy, C₁-C₆-alkylamino and di(C₁-C₆-alkyl)amino may be partially or completely halogenated and/or may carry any combination of 1, 2 or 3 radicals R^(#) and wherein C₃-C₆-cycloalkyl may carry any combination of 1, 2, 3 or 4 substituents, independently of each another being selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, halogen and R^(#), it being also possible that R^(5a) and R^(5b) or R^(5c) and R^(5d) or R^(5e) and R^(5f) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which carries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl and R^(#); it being also possible that R^(5a) and R^(5c) or R^(5d) and R^(5f) together with the carbon atoms to which they are bound form a fused 5-, 6- or 7-membered saturated, unsaturated or aromatic carbocycle, which is unsubstituted or carries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl and R^(#); R⁶ and R⁷ are selected each independently from one another from the group consisting of hydrogen, CN, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals, Ar³, —B—C(˜O)R^(a), —B—C(═S)R^(a), —B—C(═NR^(f))R^(a), —B—C(═NR^(f))OR^(b), —B—C(═NR^(f))NR^(c)R^(d), —B—C(═NR^(f))SR^(e), —B—C(═O)OR^(b), —B—C(═O)NR^(c)R^(d), —B—C(═O)SR^(e), —B—C(═S)OR^(b), —B—C(═S)NR^(c)R^(d), —B—C(═S)SR^(e), —B—OR^(b), —B—O—C(═O)R^(a), —B—O—C(═O)OR^(b), —B—O—C(═O)—NR^(c)R^(d), —B—O—C(═O)SR^(e), —B—SR^(e), —B—NR^(c)R^(d), —B—NR^(f)—C(═O)R^(a), —B—NR^(f)—C(═O)OR^(b), —B—NR^(f)—C(═O)NR^(c)R^(d), —B—N═CR^(a)R^(a)′, —B—NR^(f)—NR^(c)R^(d), —B—NR^(f)—C(═O)SR^(e), —B—NR^(f)—C(═S)NR^(c)R^(d), —B—S(═O)R^(e), —B—S(═O)₂R^(e), —S(═O)₂OR^(b), —S(═O)₂NR^(c)R^(d), —P(═O)R^(g)R^(h) and P(═S)R^(g)R^(h), wherein C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl recited in the definition of R⁶ and R⁷ may be partly or completely halogenated and/or may carry any combination of 1, 2, 3, 4 or 5 substituents R*, wherein C₃-C₈-cycloalkyl is unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 substituents selected from halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl and R*, wherein the 5-, 6- or 7-membered heterocyclic radicals contain 1, 2, 3 or 4 heteroatoms selected independently from one another from S, O and N as ring members, and wherein the 5-, 6- or 7-membered heterocyclic radicals are unsubstituted or carry any combination of 1, 2, 3, 4 or 5 substituents selected from C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, halogen and R*, B is a single bond or linear or branched C₁-C₄-alkanediyl, and R^(a), R^(a)′, R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and R^(h) independently of one another have one of the meanings given below, R* is selected from CN, NO₂, —OR^(b), —NR^(c)R^(d), —SR^(e), —C(═O)R^(a), —C(═O)OR^(b), C₃-C₈-cycloalkyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals, —Ar⁴, —O—Ar⁴, —S—Ar⁴ and —CH₂—Ar⁴, wherein the 5-, 6- or 7-membered heterocyclic radicals contain 1, 2, 3 or 4 heteroatoms selected independently from one another from S, O and N as ring members, and wherein C₃-C₈-cycloalkyl and the heterocyclic radicals are unsubstituted or carry any combination of 1, 2 or 3 or substituents, independently of one another selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl and R⁴; R^(#) is selected from C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, CN, NO₂, —OR^(b), —SR^(e), —NR^(c)R^(d), C(═O)—R^(a) and C(═O)OR^(b); R^(a), R^(a)′, R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and R^(h) are independently of one another selected from hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms selected independently from one another from O, S, N as ring members, and Ar⁵, wherein C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl may be partly or completely halogenated and/or may carry any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆: haloalkoxycarbonyl, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, Ar⁶, —CH₂—Ar⁶, —O—Ar⁶ and —S—Ar⁶, and wherein C₃-C₈-cycloalkyl and the heterocyclic radicals are unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from halogen, CN, NO₂, OH, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, Ar⁶, —CH₂—Ar⁶, —O—Ar⁶ and —S—Ar⁶; Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are independently of one another selected from phenyl, naphthyl and mono- or bicyclic 5- to 10-membered heteroaryl, which contains 1, 2, 3 or 4 heteroatoms selected from O, S and N as ring members, wherein phenyl, naphthyl and heteroaryl are unsubstituted or carry any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), which are selected from halogen, CN, NO₂, NH₂, CH₂NH₂, OH, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, unsubstituted phenyl and phenyl carrying 1, 2, 3, 4 or 5 substituents selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, and the salts thereof.
 2. The compound according to claim 1, wherein R¹ and R² are independently selected from the group consisting of halogen, CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.
 3. The compound according to claim 1, wherein m is 2 or 3 and 2 radicals R¹ are located in the 3- and 5-position, relative to the bonding position.
 4. The compound according to claim 1, wherein n is 2 or 3 and 2 radicals R² are located in the 2- and 3-position, relative to the bonding position.
 5. The compound according to claim 1, wherein the compound of formula I is selected from compounds of formula (I′)

wherein A, R³ and R⁴ are as defined in claim 1, R^(1a) and R^(1b) are independently of each other hydrogen or have one of the meanings given for R¹, R^(2a), R^(2b) and R^(2c) are independently of each other hydrogen or have one of the meanings given for R² in—claim
 1. 6. The compound according to claim 5, wherein R^(1a) is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R^(1b) is selected from the group consisting of halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R^(2a) is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R^(2b) is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl and C₁-C₃-haloalkyl; or R^(2a) together with R^(2b) forms a bivalent radical selected from the group consisting of —CH═CH—CH═CH—, —O—CH₂—CH₂—, —O—CH₂—O—, —O—CF₂—O— and —O—CH₂—CH₂—O—; and R^(2c) is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 7. The compound according to claim 6, wherein R^(2b) and R^(2c) are independently selected from the group consisting of hydrogen and C₁-C₃-alkyl.
 8. The compound according to—claim 1, wherein R³ is hydrogen or C₁-C₆-alkyl, and R⁴ is selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, and C₂-C₆-alkynyl, wherein the last 3 radicals mentioned may be partly or completely halogenated and/or may carry any combination of 1, 2 or 3 radicals selected independently of one another from the group consisting of CN, NO₂, —OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, NH₂, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, —SH and C₁-C₆-alkylthio.
 9. The compound according to claim 8, wherein R⁴ is selected from the group consisting of hydrogen, halogen and C₁-C₆-alkyl.
 10. The compound according to claim 1, wherein R³ and R⁴ are hydrogen.
 11. The compound according to claim 1, wherein R^(5e) and R^(5f) are hydrogen.
 12. The compound according to claim 1, wherein R^(5a), R^(5b), R^(5c), and R^(5d), independently of one another, are selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), wherein R^(Ar), it being possible that either R^(5a) and R^(5b) or R^(5C) and R^(5d) or R^(5e) and R^(5f) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which carries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.
 13. The compound according to claim 12, wherein R^(5a), R^(5b), R^(5C) and R^(5d) are hydrogen, or 1 or 2 of the radicals R^(5a), R^(5b), R^(5C) and R^(5d) are selected from the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and phenyl, which is unsubstituted or carries any combination of 1, 2, 3, 4 or 5 substituents R^(Ar), or either R^(5a) and R^(5b) or R^(5c) and R^(5d) or R^(5e) and R^(5f) together with the carbon atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated carbocycle, which is unsubstituted or which caries any combination of 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl, while the remaining radicals R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) or R^(5f) are hydrogen.
 14. The compound according to claim 1, wherein R^(5a), R^(5b), R^(5c), R^(5d), R^(5e) and R^(5f) are hydrogen.
 15. The compound according to claim 1, wherein R⁶ and R⁷, independently of one another, are selected from the group consisting of hydrogen, CN, NO₂, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, B—C(═O)R^(a), —B—C(═O)OR^(b), —B—C(═O)SR^(e), —B—C(═S)OR^(b), —B—C(═S)NR^(c)R^(d), —B—C(═S)SR^(e), —B—OR^(b), —B—SR^(e), —S(═O)R^(e), —B—NR^(c)R^(d), —S(═O)₂R^(e) and —S(═O)₂OR^(b), wherein C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl may be partly or completely halogenated and/or may carry any combination of 1, 2, 3, 4 or 5 substituents, independently of one another selected from the group consisting of CN, NO₂, —OH, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, —SH, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —C(═O)H, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms selected independently from one another from the group consisting of O, S, and N as ring members, and —Ar⁴, wherein C₃-C₈-cycloalkyl is unsubstituted or may carry any combination of 1, 2, 3 or 4 substituents, independently of one another selected from the group consisting of halogen, CN, NO₂, —OH, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, —SH, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —C(═O)H, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, saturated or partially unsaturated 5-, 6- or 7-membered heterocyclic radicals containing 1, 2, 3 or 4 heteroatoms selected independently from one another from the group consisting of O, S, and N as ring members, —Ar⁴ and —CH₂—Ar⁴— wherein B is a single bond or —CH₂—, and wherein R^(a), R^(b), R^(c), R^(d) and R^(e), independently of one another, have one of the meanings given in claim
 1. 16. The compound according to claim 15, wherein R⁶ and R⁷, independently of one another, are selected from the group consisting of hydrogen, CN, C₁-C₆-alkyl, —C(═O)R^(a), —C(═O)OR^(b), —OR^(b) and —B—NR^(c)R^(d), wherein C₁-C₆-alkyl may be partly or completely halogenated and/or may carry any combination of 1, 2, or 3 substituents, independently of one another selected from the group consisting of CN, NO₂, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio and wherein B is a single bond or —CH₂—, and wherein R^(a), R^(b), R^(c) and R^(d) are selected independently of one another from the group consisting of hydrogen, C₁-C₆-alkyl and phenyl wherein phenyl is unsubstituted or carries 1, 2, 3, 4 or 5 substituents, independently of one another selected from the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.
 17. The compound according to claim 16, wherein R⁶ and R⁷ are hydrogen.
 18. An agricultural composition containing at least one compound of claim 1 and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
 19. A method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or plants, plant propagation materials, soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of claim 1 or a salt thereof.
 20. The method as claimed in claim 18, for protecting plant propagation material and/or the plants which grow therefrom, which method comprises treating the seed with a pesticidally effective amount of a compound of claim 1 and/or an agriculturally acceptable salt thereof.
 21. Plant propagation material, comprising at least one compound of claim 1 and/or an agriculturally acceptable salt thereof.
 22. A method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of claim 1 and/or a veterinally acceptable salt thereof. 